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CAS 427-49-6

2-cyclopentyl-2-hydroxy-2-phenylacetic acid(+/-)-Cyclopentylmandelic acid

Codes: GLYC-004, (I)860865-1-a, SOFBR-003, LPHE-006

Application context (from source-drug indications)

AsthmaBudesonide/Formoterol fumarate/Glycopyrronium BromideChronic obstructive pulmonary diseaseBudesonide/Formoterol fumarate/Glycopyrronium BromideHyperhidrosisGlycopyrrolate TosylateChronic obstructive pulmonary diseaseGlycopyrrolate TosylateAsthmaGlycopyrrolate TosylateChronic obstructive pulmonary diseaseFormoterol Fumarate/GlycopyrrolateChronic obstructive pulmonary diseaseIndacaterol Maleate/Glycopyrronium BromideSialorrhoeaGlycopyrronium BromideChronic obstructive pulmonary diseaseGlycopyrronium BromideDuodenal ulcerGlycopyrronium BromideGastric ulcerGlycopyrronium BromideGastritisGlycopyrronium BromideAnaesthesiaGlycopyrronium BromideHyperhidrosisSofpironium Bromide晕动病L-Phencynonate HydrochlorideCerebral infarctionL-Phencynonate HydrochlorideVertigoL-Phencynonate Hydrochloride

Source drugs (routes using this intermediate)

DrugTierExpiry
Budesonide/Formoterol fumarate/Glycopyrronium BromideTier B — Position early-
Glycopyrrolate TosylateTier C — Watch / trade-
Formoterol Fumarate/GlycopyrrolateTier C — Watch / trade-
Indacaterol Maleate/Glycopyrronium BromideTier B — Position early-
Glycopyrronium BromideTier C — Watch / trade-
Sofpironium BromideTier C — Watch / trade-
L-Phencynonate HydrochlorideTier C — Watch / trade-

Position in synthesis routes (up/downstream chain)

Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.

Budesonide/Formoterol fumarate/Glycopyrronium BromideOriginator routesteps: 4total yield: 22.7 g
methyl 2-oxo-2-phenylacetate→bromocyclopentane→methyl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-cyclopentyl-2-hydroxy-2-phenylacetic acid→1-methylpyrrolidin-3-ol→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate
Budesonide/Formoterol fumarate/Glycopyrronium BromideOptimised routesteps: 3total yield: 361 g
2-cyclopentyl-2-hydroxy-2-phenylacetic acid→1-methylpyrrolidin-3-ol→2-chloro-4,6-dimethoxy-1,3,5-triazine→4,6-dimethoxy-1,3,5-triazin-2-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate
Budesonide/Formoterol fumarate/Glycopyrronium BromideOptimised routesteps: 4total yield: 144 g (Glycopyrronium Bromide)
2-cyclopentyl-2-hydroxy-2-phenylacetic acid→1-methylpyrrolidin-3-ol→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-(benzyloxy)-2-cyclopentyl-2-phenylacetic acid→1-methylpyrrolidin-3-yl 2-(benzyloxy)-2-cyclopentyl-2-phenylacetate
Budesonide/Formoterol fumarate/Glycopyrronium BromideOptimised routesteps: 4total yield: 3.9 g (Glycopyrronium Bromide)
bromocyclopentane→methyl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-cyclopentyl-2-hydroxy-2-phenylacetic acid→1-methylpyrrolidin-3-ol→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-oxo-2-phenylacetic acid
Glycopyrrolate TosylateOptimised routesteps: 4total yield: /
(+/-)-Cyclopentylmandelic acid→2-Cyclopentyl-2-hydroxy-1-(1H-imidazol-1-yl)-2-phenylethanone→1-Methylpyrrolidin-3-ol→(1-Methylpyrrolidin-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate→(3R)-1-Methylpyrrolidin-3-yl (2S)-cyclopentyl(hydroxy)phenylacetate→4-Methylbenzenesulfonic acid methyl ester
Formoterol Fumarate/GlycopyrrolateOptimised routesteps: 4total yield: /
(+/-)-Cyclopentylmandelic acid→2-Cyclopentyl-2-hydroxy-1-(1H-imidazol-1-yl)-2-phenylethanone→1-Methylpyrrolidin-3-ol→(1-Methylpyrrolidin-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate→(3R)-1-Methylpyrrolidin-3-yl (2S)-cyclopentyl(hydroxy)phenylacetate→4-Methylbenzenesulfonic acid methyl ester
Indacaterol Maleate/Glycopyrronium BromideOriginator routesteps: 4total yield: 22.7 g
methyl 2-oxo-2-phenylacetate→bromocyclopentane→methyl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-cyclopentyl-2-hydroxy-2-phenylacetic acid→1-methylpyrrolidin-3-ol→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate
Indacaterol Maleate/Glycopyrronium BromideOptimised routesteps: 3total yield: 361 g
2-cyclopentyl-2-hydroxy-2-phenylacetic acid→1-methylpyrrolidin-3-ol→2-chloro-4,6-dimethoxy-1,3,5-triazine→4,6-dimethoxy-1,3,5-triazin-2-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate
Indacaterol Maleate/Glycopyrronium BromideOptimised routesteps: 4total yield: 144 g (Glycopyrronium Bromide)
2-cyclopentyl-2-hydroxy-2-phenylacetic acid→1-methylpyrrolidin-3-ol→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-(benzyloxy)-2-cyclopentyl-2-phenylacetic acid→1-methylpyrrolidin-3-yl 2-(benzyloxy)-2-cyclopentyl-2-phenylacetate
Indacaterol Maleate/Glycopyrronium BromideOptimised routesteps: 4total yield: 3.9 g (Glycopyrronium Bromide)
bromocyclopentane→methyl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-cyclopentyl-2-hydroxy-2-phenylacetic acid→1-methylpyrrolidin-3-ol→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-oxo-2-phenylacetic acid
Glycopyrronium BromideOriginator routesteps: 4total yield: 22.7 g
methyl 2-oxo-2-phenylacetate→bromocyclopentane→methyl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-cyclopentyl-2-hydroxy-2-phenylacetic acid→1-methylpyrrolidin-3-ol→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate
Glycopyrronium BromideOptimised routesteps: 3total yield: 361 g
2-cyclopentyl-2-hydroxy-2-phenylacetic acid→1-methylpyrrolidin-3-ol→2-chloro-4,6-dimethoxy-1,3,5-triazine→4,6-dimethoxy-1,3,5-triazin-2-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate
Glycopyrronium BromideOptimised routesteps: 4total yield: 144 g (Glycopyrronium Bromide)
2-cyclopentyl-2-hydroxy-2-phenylacetic acid→1-methylpyrrolidin-3-ol→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-(benzyloxy)-2-cyclopentyl-2-phenylacetic acid→1-methylpyrrolidin-3-yl 2-(benzyloxy)-2-cyclopentyl-2-phenylacetate
Glycopyrronium BromideOptimised routesteps: 4total yield: 3.9 g (Glycopyrronium Bromide)
bromocyclopentane→methyl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-cyclopentyl-2-hydroxy-2-phenylacetic acid→1-methylpyrrolidin-3-ol→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-oxo-2-phenylacetic acid
Sofpironium BromideOriginator routesteps: 4total yield: /
2-oxo-2-phenylacetic acid→cyclopentylmagnesium bromide→2-cyclopentyl-2-hydroxy-2-phenylacetic acid→(R)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid→(R)-1-methylpyrrolidin-3-ol→(R)-1-methylpyrrolidin-3-yl (R)-2-cyclopentyl-2-hydroxy-2-phenylacetate→(3R)-3-((R)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1-(2-ethoxy-2-oxoethyl)-1-methylpyrrolidin-1-ium bromide
L-Phencynonate HydrochlorideOriginator routesteps: 7total yield: /
cyclopentylmagnesium bromide→diethyl oxalate→ethyl 2-cyclopentyl-2-oxoacetate→phenylmagnesium bromide→ethyl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-cyclopentyl-2-hydroxy-2-phenylacetic acid→(S)-1-phenylpropan-2-amine→(S)-1-phenylpropan-2-amine (R)-2-cyclopentyl-2-hydroxy-2-phenylacetate→(R)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid→(R)-methyl 2-cyclopentyl-2-hydroxy-2-phenylacetate→(1R,5S,9s)-3-methyl-3-azabicyclo[3.3.1]nonan-9-ol

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