HCID 57486904, compound → tert-butyl N-[(3R,4S)-3-hydroxypiperidin-4-yl]carbamate

HRID 1782021Notes

Reaction equation

HRID 1782021 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:13]([OH:25])[CH2:12]1)=O)C1C=CC=CC=1>CO>[C:21]([O:20][C:18](=[O:19])[NH:17][C@H:14]1[CH2:15][CH2:16][NH:11][CH2:12][C@H:13]1[OH:25])([CH3:24])([CH3:22])[CH3:23]

Participants

3

Reactant 1

HCID 57486904HCID 57486904, compound

Product 1

HCID 67426921tert-butyl N-[(3R,4S)-3-hydroxypiperidin-4-yl]carbamateYield 100.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10.0 g of cis-4-tert-Butoxycarbonylamino-3-hydroxy-piperidine-1-carboxylic acid benzyl ester slow running Isomer 2 (10b), was dissolved in methanol (350 mL) and was degassed. Pearlman's catalyst (palladium hydroxide on carbon, 20wt % Pd (dry basis), ≦50% water, 500 mg) was added and the mixture was purged with hydrogen and stirring continued under a balloon of hydrogen for 12 hours. The mixture was degassed with argon, filtered through a pad of Celite, and evaporated to dryness to afford 6.2 g (100%) of a white solid.

Workup

  1. customwas degassed
  2. additionPearlman's catalyst (palladium hydroxide on carbon, 20wt % Pd (dry basis), ≦50% water, 500 mg) was added
  3. customthe mixture was purged with hydrogen
  4. customThe mixture was degassed with argon
  5. filtrationfiltered through a pad of Celite
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-bd056aa6698646c688e0db6a8fc59919
Source dataset
uspto-grants-2009_03
Patent number
US07498326B2

Reaction notes

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