(S)-benzyl 4-(3-(tert-butoxycarbonylamino)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate → (S)-tert-butyl 2-oxo-1-(piperidin-4-yl)pyrrolidin-3-ylcarbamate

HRID 407995Notes

Reaction equation

HRID 407995 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][N:17](C(OCC3C=CC=CC=3)=O)[CH2:16][CH2:15]2)[C:10]1=[O:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[O:30]=[C:10]1[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][CH2:12][N:11]1[CH:14]1[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 86688075(S)-benzyl 4-(3-(tert-butoxycarbonylamino)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86688117(S)-tert-butyl 2-oxo-1-(piperidin-4-yl)pyrrolidin-3-ylcarbamateYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-benzyl 4-(3-(tert-butoxycarbonylamino)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (Preparation E, Step C, 7.0 g, 17 mmol) in methanol (300 mL) purged with nitrogen was added Pd/C (10%, 2 g) and the reaction was stirred overnight at ambient temperature under a balloon of hydrogen gas. The reaction was next purged with nitrogen and filtered through Celite®, and the filter cake was washed with methanol (about 100 mL). The combined organic phases were concentrated under vacuum to yield (S)-tert-butyl 2-oxo-1-(piperidin-4-yl)pyrrolidin-3-ylcarbamate (4.0 g, 83%)

Workup

  1. customThe reaction was next purged with nitrogen
  2. filtrationfiltered through Celite®
  3. washthe filter cake was washed with methanol (about 100 mL)
  4. concentrationThe combined organic phases were concentrated under vacuum

Sources & evidence

ORD record
ord-265402a67edd4d03bff8d83d96d0244d
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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