Diazomethane → (3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-cyclopropylpyrrolidine

HRID 1253424Notes

Reaction equation

HRID 1253424 reaction equation
[N+](=[CH2:3])=[N-].[CH2:4]([O:11][C:12]([N:14]1[CH2:18][C@H:17]([CH:19]=[CH2:20])[C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:15]1)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:4]([O:11][C:12]([N:14]1[CH2:18][C@H:17]([CH:19]2[CH2:3][CH2:20]2)[C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:15]1)=[O:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 59665269(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidine

Product 1

HCID 53837949(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-cyclopropylpyrrolidine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

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%).

Workup

  1. additionwas added
  2. customAfter completion of reaction, insoluble matter
  3. customwas removed through filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe obtained residue was purified though silica gel column chromatography (ethyl acetate:n-hexane=1:9 to 1:4)

Sources & evidence

ORD record
ord-769fa2b046694926a4ebc77edee1f8c6
Source dataset
uspto-grants-2013_06
Patent number
US08455482B2

Reaction notes

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