4-(2-Benzyloxycarbonylamino-3-methyl-butyryl)-3-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester → 4-(2-Amino-3-methyl-butyryl)-3-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

HRID 1965162Notes

Reaction equation

HRID 1965162 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]2[N:20]([C:23](=[O:39])[CH:24]([NH:28]C(OCC3C=CC=CC=3)=O)[CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:22][CH:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:10]2[N:20]([C:23](=[O:39])[CH:24]([NH2:28])[CH:25]([CH3:26])[CH3:27])[CH2:21][CH2:22][CH:9]12)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 1

HCID 676063944-(2-Benzyloxycarbonylamino-3-methyl-butyryl)-3-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

Product 1

HCID 676088584-(2-Amino-3-methyl-butyryl)-3-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 500 mL Parr bottle was charged with crude 14 (410 mg, 0.76 mmol) and 10% Pd-on-carbon (50 mg) in reagent grade MeOH (10 mL). The mixture was pressurized to 50 PSI H2 then shaken for 2 h. The catalyst was removed by filtration through Celite® and the solids were washed with MeOH and EtOAc. The filtrate was concentrated in vacuo to afford 307 mg (quant.) of 15 which was used without further purification.

Workup

  1. customThe catalyst was removed by filtration through Celite®
  2. washthe solids were washed with MeOH and EtOAc
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bc0751787bea4da3af10edaf65e72ce7
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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