1-benzyloxycarbonyl-3-(R)-[1-[N-(tert-butoxycarbonyl)-N-(methyl)Amino]Cyclopropyl]Pyrrolidine → tert-Butyl methyl{1-[(3R)-pyrrolidin-3-yl]cyclopropyl}carbamate

HRID 600898Notes

Reaction equation

HRID 600898 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][C@@H:13]([C:16]2([N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH3:20])[CH2:18][CH2:17]2)[CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[C].[Pd]>[C:24]([O:23][C:21]([N:19]([C:16]1([C@@H:13]2[CH2:14][CH2:15][NH:11][CH2:12]2)[CH2:18][CH2:17]1)[CH3:20])=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

4

Reactant 1

HCID 229403761-benzyloxycarbonyl-3-(R)-[1-[N-(tert-butoxycarbonyl)-N-(methyl)Amino]Cyclopropyl]Pyrrolidine

Product 1

HCID 67271848tert-Butyl methyl{1-[(3R)-pyrrolidin-3-yl]cyclopropyl}carbamate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

1-benzyloxycarbonyl-3-(R)-[1-[N-(tert-butoxycarbonyl)-N-(methyl)amino]cyclopropyl]pyrrolidine (1.31 g, 3.48 mmol) was dissolved in ethanol (13 ml), and after adding a 10% palladium carbon catalyst (water content: 50%; 0.65 g) thereto, it was stirred at room temperature for 5 hours under a hydrogen atmosphere at atmospheric pressure. After performing filtration through cellite (ethanol washing), the filtrate was concentrated under a reduced pressure. As a result, 0.92 g (quantitative) of the title compound was obtained in the form of a colorless syrup.

Workup

  1. filtrationfiltration through cellite (ethanol washing)
  2. concentrationthe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-cd6272a50cb147ce8868c78872da3d37
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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