HCID 59904582, compound → HCID 59904579, compound

HRID 2303395Notes

Reaction equation

HRID 2303395 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C@:14]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([OH:17])[C@@H:13]([OH:25])[CH2:12]1)=O)C1C=CC=CC=1>CCO.[Pd]>[CH2:18]([C@:14]1([OH:17])[CH2:15][CH2:16][NH:11][CH2:12][C@@H:13]1[OH:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 59904582HCID 59904582, compound

Product 1

HCID 59904579HCID 59904579, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(3R,4R) and (3S,4S)-4-Benzyl-3,4-dihydroxy-piperidine-1-carboxylic acid benzyl ester 1.46 g (4.3 mmol) was dissolved in 30 ml EtOH and hydrogenated in the presence of 400 mg Pd/C (10%) under atmospheric pressure of H2 at r.t. After 16 hours the reaction was complete and the catalyst was filtered off and the solvent was removed under reduced pressure to give 796 mg (3.8 mmol, 89%) (3R,4R) and (3S,4S)-4-benzyl-3,4-dihydroxy-piperidine as an oil.

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f5e79b2c44b94b08ad31b0aeaed7f8f5
Source dataset
uspto-grants-2002_08
Patent number
US06432985B1

Reaction notes

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