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

HRID 1010562
Notes
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Reaction equation

HRID 1010562 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 Ether
Solvent

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 mmol). 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-adb8be1ebc5e4f6db1dfa290b564b6d8
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977327B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes