HCID 67309147, compound → HCID 67308469, compound

HRID 1010564Notes

Reaction equation

HRID 1010564 reaction equation
C(OC([N:11]1[CH2:15][CH:14]([C:16]([CH3:18])=[CH2:17])[C@H:13]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>[C].[Pd].CO>[C:23]([O:22][C:20]([NH:19][C@H:13]1[CH:14]([CH:16]([CH3:18])[CH3:17])[CH2:15][NH:11][CH2:12]1)=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 67309147HCID 67309147, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67308469HCID 67308469, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A 10% palladium carbon catalyst (300 mg) was added to a solution of (3S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-isopropenylpyrrolidine (300 mg, 832 μmol) in methanol (10 mL), and the resultant mixture was stirred in a hydrogen atmosphere under an ordinary pressure for 2 hours. After filtration, a 10% palladium carbon catalyst (300 mg) was added again to the filtrate, followed by stirring in a hydrogen atmosphere under an ordinary pressure for 1 hour. After filtration, the filtrate was concentrated under reduced pressure, to thereby yield (3S)-3-(tert-butoxycarbonyl)amino-4-isopropylpyrrolidine as a colorless amorphous (172 mg, quantitative amount).

Workup

  1. filtrationAfter filtration
  2. additiona 10% palladium carbon catalyst (300 mg) was added again to the filtrate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-571ccf174f3640fa8f1beac9d44ce622
Source dataset
uspto-grants-2011_07
Patent number
US07977327B2

Reaction notes

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