Benzyl chloroformate → (3R)-1-Benzyloxycarbonyl-3-(1-tert-butoxycarbonylaminocyclopropyl)pyrrolidine

HRID 600896Notes

Reaction equation

HRID 600896 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C@@H:12]2[CH2:16][CH2:15][N:14]([C@H](C3C=CC=CC=3)C)[CH2:13]2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:25]([O:32][C:33](Cl)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[CH2:25]([O:32][C:33]([N:14]1[CH2:15][CH2:16][C@@H:12]([C:9]2([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:11][CH2:10]2)[CH2:13]1)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 672715733-(R)-[1-(tert-butoxycarbonylamino)cyclopropyl]-1-[1-(S)-phenylethyl]Pyrrolidine

Product 1

HCID 11132144(3R)-1-Benzyloxycarbonyl-3-(1-tert-butoxycarbonylaminocyclopropyl)pyrrolidineYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(R)-[1-(tert-butoxycarbonylamino)cyclopropyl]-1-[1-(S)-phenylethyl]pyrrolidine (1.70 g, 5.15 mmol) was dissolved in dichloromethane (34 ml), and benzylchloroformate (1.10 ml, 7.73 mmol) was added dropwise while stirring and cooling with ice. The reaction solution was then stirred at room temperature for 2.5 hours and then stirred at 40° C. for 1.5 hours. After letting the reaction solution cool, the reaction solution was concentrated under a reduced pressure, the concentrate was applied to a silica gel chromatography, and 1.40 g (75%) of the title compound was obtained in the form of a colorless syrup from an n-hexane:ethyl acetate=2:1 eluate. The instrumental analysis data for this resulting compound agreed with the data indicated in PCT/JP96/00208.

Workup

  1. temperaturecooling with ice
  2. stirringThe reaction solution was then stirred at room temperature for 2.5 hours
  3. stirringstirred at 40° C. for 1.5 hours
  4. temperaturecool
  5. concentrationthe reaction solution was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-56ce2e345b09413cb647d5e8607a249f
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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