3-Phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester → 3-Phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

HRID 1965160Notes

Reaction equation

HRID 1965160 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(OCC3C=CC=CC=3)=O)[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[NH:20][CH2:21][CH2:22][CH:9]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 676086123-Phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

Product 1

HCID 675137713-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 12 (370 mg, 0.84 mmol) and 5% Pd-on-carbon (50 mg) in reagent grade MeOH (10 mL). The mixture was pressurized to 50 PSI H2 then shaken for 1 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 256 mg (quant.) of 13 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-d0aca1a1b5cd414cad83e9b047184c45
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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