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CAS 13118-11-1
1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate(1-Methylpyrrolidin-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate
Codes: GLYC-006, (IV)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.
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
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
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
(+/-)-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
(+/-)-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
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
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
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)
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
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
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
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
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
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
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