CAS 13220-33-2

1-methylpyrrolidin-3-ol1-Methylpyrrolidin-3-ol

Codes: GLYC-005, (III)860865-1-a

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 Bromide

Source drugs (routes using this intermediate)

Drug	Tier	Expiry
Budesonide/Formoterol fumarate/Glycopyrronium Bromide	Tier B — Position early	-
Glycopyrrolate Tosylate	Tier C — Watch / trade	-
Formoterol Fumarate/Glycopyrrolate	Tier C — Watch / trade	-
Indacaterol Maleate/Glycopyrronium Bromide	Tier B — Position early	-
Glycopyrronium Bromide	Tier 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: 3total yield: /

1-methylpyrrolidin-3-ol→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-cyclopentyl-2-oxoacetic acid→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-oxoacetate→bromobenzene

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: /

Indacaterol Maleate/Glycopyrronium BromideOriginator routesteps: 4total yield: 22.7 g

Indacaterol Maleate/Glycopyrronium BromideOptimised routesteps: 3total yield: 361 g

Indacaterol Maleate/Glycopyrronium BromideOptimised routesteps: 3total yield: /

1-methylpyrrolidin-3-ol→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-cyclopentyl-2-oxoacetic acid→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-oxoacetate→bromobenzene

Indacaterol Maleate/Glycopyrronium BromideOptimised routesteps: 4total yield: 144 g (Glycopyrronium Bromide)

Indacaterol Maleate/Glycopyrronium BromideOptimised routesteps: 4total yield: 3.9 g (Glycopyrronium Bromide)

Glycopyrronium BromideOriginator routesteps: 4total yield: 22.7 g

Glycopyrronium BromideOptimised routesteps: 3total yield: 361 g

Glycopyrronium BromideOptimised routesteps: 3total yield: /

1-methylpyrrolidin-3-ol→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate→2-cyclopentyl-2-oxoacetic acid→1-methylpyrrolidin-3-yl 2-cyclopentyl-2-oxoacetate→bromobenzene

Glycopyrronium BromideOptimised routesteps: 4total yield: 144 g (Glycopyrronium Bromide)

Glycopyrronium BromideOptimised routesteps: 4total yield: 3.9 g (Glycopyrronium Bromide)

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