HCID 69758881, compound → HCID 10154506, compound

HRID 2303401Notes

Reaction equation

HRID 2303401 reaction equation
[CH2:1]([C@:8]1([OH:32])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([O:23]CC3C=CC=CC=3)=[CH:19][CH:18]=2)[CH2:10][C@@H:9]1[OH:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCO.[Pd]>[CH2:1]([C@:8]1([OH:32])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)[CH2:10][C@@H:9]1[OH:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 69758881HCID 69758881, compound

Product 1

HCID 10154506HCID 10154506, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(3R,4R) and (3 S,4S)-4-benzyl-1-[2-(4-benzyloxy-phenoxy)-ethyl]-piperidine-3,4-diol 550 mg (1.3 mmol) was dissolved in 10 ml EtOH and hydrogenated in the presence of 100 mg Pd/C (10%) under atmospheric pressure at 50° C. After 4 hours the reaction was complete and the catalyst was filtered off and the solvent was removed under reduced pressure to give the crude product. Purification by chromatography (CH2Cl2/MeOH 9:1) yielded 249 mg (0.73 mmol, 56%) (3R,4R) and (3S,4S)-4-benzyl-1-[2-(4-hydroxy-phenoxy)-ethyl]-piperidine-3,4-diol as a solid.

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe solvent was removed under reduced pressure
  3. customto give the crude product
  4. customPurification by chromatography (CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-abccca67c07b4aa8bf0fc9cfb7f264df
Source dataset
uspto-grants-2002_08
Patent number
US06432985B1

Reaction notes

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