tert-Butyl 4-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-3,3-dimethylpiperidine-1-carboxylate → tert-butyl 4-((S)-3-amino-2-oxopyrrolidin-1-yl)-3,3-dimethylpiperidine-1-carboxylate

HRID 408023Notes

Reaction equation

HRID 408023 reaction equation
C(OC([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][C:18]2([CH3:31])[CH3:30])[C:13]1=[O:32])=O)C1C=CC=CC=1>CO>[NH2:11][C@H:12]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:19][C:18]2([CH3:31])[CH3:30])[C:13]1=[O:32]

Participants

3

Reactant 1

HCID 67469782tert-Butyl 4-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-3,3-dimethylpiperidine-1-carboxylate

Product 1

HCID 67469742tert-butyl 4-((S)-3-amino-2-oxopyrrolidin-1-yl)-3,3-dimethylpiperidine-1-carboxylateYield 105.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 4-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-3,3-dimethylpiperidine-1-carboxylate (0.81 g, 1.8 mmol) was dissolved in methanol (20 mL) and the mixture was purged with N2 by three vacuum pump/N2 balloon cycles. 10% Palladium on carbon (dry basis, wet, Degussa type, 0.5 g) was added and the system was purged with 1 atm H2 by three vacuum pump/H2 balloon cycles. The reaction was stirred under the H2 atmosphere until the starting material was consumed. The mixture was filtered through Celite® and concentrated to afford tert-butyl 4-((S)-3-amino-2-oxopyrrolidin-1-yl)-3,3-dimethylpiperidine-1-carboxylate (0.59 g, 1.9 mmol, 100% yield) as a white solid.

Workup

  1. customthe mixture was purged with N2 by three vacuum pump/N2 balloon cycles
  2. addition10% Palladium on carbon (dry basis, wet, Degussa type, 0.5 g) was added
  3. customthe system was purged with 1 atm H2 by three vacuum pump/H2 balloon cycles
  4. customwas consumed
  5. filtrationThe mixture was filtered through Celite®
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b9996ab053364a1abe2f9733185c8d19
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

Loading…