{1-[6-(3,4-Difluoro-phenoxy)-4-(tetrahydro-pyran-4-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid benzyl ester → 2-Amino-1-[6-(3,4-difluoro-phenoxy)-4-(tetrahydro-pyran-4-yl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-3,3-dimethyl-butan-1-one

HRID 1965171Notes

Reaction equation

HRID 1965171 reaction equation
C(OC(=O)[NH:10][CH:11]([C:16]([N:18]1[CH2:22][CH2:21][CH:20]2[N:23]([CH:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[CH2:24][CH:25]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([F:34])[CH:28]=3)[CH:19]12)=[O:17])[C:12]([CH3:15])([CH3:14])[CH3:13])C1C=CC=CC=1>CO>[NH2:10][CH:11]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:16]([N:18]1[CH2:22][CH2:21][CH:20]2[N:23]([CH:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[CH2:24][CH:25]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([F:34])[CH:28]=3)[CH:19]12)=[O:17]

Participants

3

Reactant 1

HCID 67607614{1-[6-(3,4-Difluoro-phenoxy)-4-(tetrahydro-pyran-4-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid benzyl ester

Product 1

HCID 675142402-Amino-1-[6-(3,4-difluoro-phenoxy)-4-(tetrahydro-pyran-4-yl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-3,3-dimethyl-butan-1-oneYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of carbamate 25 (170 mg, 0.30 mmol) and 10% Pd-on-carbon (wet, 100 mg, 0.09 mmol) in MeOH (20 mL) was stirred vigorously under 1 atm H2 for 2.5 h. The catalyst was removed by filtration with an Acrodisc® 0.45 μm nylon membrane syringe filter and the solvent was removed in vacuo to afford 125 mg (96%) of 26 as an oil which was carried on without further purification. Mass spectrum, m/z [437.9] (M+H)+.

Workup

  1. customThe catalyst was removed by filtration with an Acrodisc® 0.45 μm nylon membrane syringe
  2. filtrationfilter
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4f1662495a9e4fb386a618512ed6be71
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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