HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Butyn-1-yl chloroformate → but-2-ynyl 3-[4-[(3aS,7aS)-2-oxo-3a,4,5,6,7,7a-hexahydro-3H-benzimidazol-1-yl]-1-piperidyl]-3-methyl-pyrrolidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Butyn-1-yl chloroformate | HCID 4131669 | — |
| Reactant | (3aS,7aS)-1-[1-(3-methylpyrrolidin-3-yl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-3H-benzoimidazol-2-one | HCID 57619793 | — |
| Product | but-2-ynyl 3-[4-[(3aS,7aS)-2-oxo-3a,4,5,6,7,7a-hexahydro-3H-benzimidazol-1-yl]-1-piperidyl]-3-methyl-pyrrolidine-1-carboxylate | HCID 25221450 | 33.9% |
Reaction Steps
Following the procedure used in example 16 and starting from (3aS,7aS)-3-[1-(3-methylpyrrolidin-3-yl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-2-one (HCl salt, 0.6 g, 1.75 mmol) and but-2-ynyl chloroformate (0.218 mL, 1.92 mmol), the title compound (0.239 g, 33.9%) was obtained after purification by preparative LC/MS (high pH) as a mixture of diastereomers. MS (M+1): 403.3
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08119661B2 |
| Source dataset | uspto-grants-2012_02 |
| ORD ID | ord-28fa545b4ff6403081d920b300f3a48a |
| Source note | uspto-grants-2012_02 |