Reaction #1340606

ord-769fa2b046694926a4ebc77edee1f8c6

Reaction equation

C=[N+]=[N-]
diazomethane
C=C[C@H]1CN(C(=O)OCc2ccccc2)C[C@H]1NC(=O)OC(C)(C)C
(3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidine
→
CC(C)(C)OC(=O)N[C@@H]1CN(C(=O)OCc2ccccc2)C[C@@H]1C1CC1
title compound
CC(C)(C)OC(=O)N[C@@H]1CN(C(=O)OCc2ccccc2)C[C@@H]1C1CC1
(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-cyclopropylpyrrolidine

Reactants

C=[N+]=[N-]
diazomethane
C=C[C@H]1CN(C(=O)OCc2ccccc2)C[C@H]1NC(=O)OC(C)(C)C
(3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidine

Reagents

CC(=O)[O-].CC(=O)[O-].[Pd+2]
palladium acetate

Solvents

CCOCC
diethyl ether

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwas added
  2. 2
    OtherAfter completion of reaction, insoluble matter
  3. 3
    Otherwas removed through filtration
  4. 4
    ConcentrationThe filtrate was concentrated under reduced pressure
  5. 5
    Otherthe obtained residue was purified though silica gel column chromatography (ethyl acetate:n-hexane=1:9 to 1:4)

Procedure

An excessive amount of a solution of diazomethane in diethyl ether (30 mL) was added to (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidine (270 mg, 779 μmol). Under cooling with ice, palladium acetate (10 mg) was added thereto, followed by stirring at room temperature for 2 hours. After completion of reaction, insoluble matter was removed through filtration. The filtrate was concentrated under reduced pressure, and the obtained residue was purified though silica gel column chromatography (ethyl acetate:n-hexane=1:9 to 1:4), to thereby yield the title compound as a colorless oily substance (269 mg, 96%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08455482B2uspto-grants-2013_06