Benzyl chloroformate → 1-Benzyloxycarbonyl-3-[1-(tert-butoxycarbonyl)amino-1-cyclopropyl]methylpyrrolidine

HRID 1368069Notes

Reaction equation

HRID 1368069 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([CH2:12][CH:13]2[CH2:17][CH2:16][N:15]([C@@H](C3C=CC=CC=3)C)[CH2:14]2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]>ClCCl>[CH2:30]([O:29][C:27]([N:15]1[CH2:16][CH2:17][CH:13]([CH2:12][C:9]2([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH2:11]2)[CH2:14]1)=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 210874423-[1-(tert-Butoxycarbonyl)amino-1-cyclopropyl]methyl-1-[1-(R)-phenylethyl]pyrrolidine

Product 1

HCID 226339261-Benzyloxycarbonyl-3-[1-(tert-butoxycarbonyl)amino-1-cyclopropyl]methylpyrrolidineYield 71.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[1-(tert-Butoxycarbonyl)amino-1-cyclopropyl]methyl-1-[1-(R)-phenylethyl]pyrrolidine (1.234 g, 3.582 mmol) was dissolved in dry dichloromethane (20 ml) to which, under ice-cooling, was subsequently added dropwise benzyl chloroformate (1278 μl, 8.955 mmol). After 8 hours of stirring at room temperature, the reaction solution was concentrated under a reduced pressure. The thus obtained residue was applied to a flash silica gel chromatography and eluted with n-hexane:ethyl acetate=2:1, thereby obtaining 959 mg (71.5%) of the title compound as a colorless oil.

Workup

  1. temperaturecooling
  2. concentrationthe reaction solution was concentrated under a reduced pressure
  3. washeluted with n-hexane

Sources & evidence

ORD record
ord-f19e5cb684c54e9584ee29e5ea871d23
Source dataset
uspto-grants-2003_06
Patent number
US06573260B1

Reaction notes

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