HCID 22628341, compound → HCID 22628407, compound

HRID 278412Notes

Reaction equation

HRID 278412 reaction equation
C([O:8][C:9]1([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[CH2:14][CH2:13][N:12]([CH2:15][CH:16]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([OH:25])[CH:22]=3)[CH:17]2[OH:26])[CH2:11][CH2:10]1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[CH2:14][CH2:13][N:12]([CH2:15][CH:16]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([OH:25])[CH:22]=3)[CH:17]2[OH:26])[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 22628341HCID 22628341, compound

Product 1

HCID 22628407HCID 22628407, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (1RS,2RS)and (1RS,2SR)-2-[4-benzyloxy-4-(4-methyl-benzyl)-piperidine-1-ylmethyl]-indan-1,5-diol (0.83 g, 1.82 mmol) in MeOH (100 ml) and Pd/C 10% (100 mg) was stirred vigorously under a hydrogen atmosphere for 1 hr at ambient temperature. After removal of the catalyst and evaporation of the solvent the title compound (1RS,2RS) and (1RS, 2SR)-2-[4-hydroxy-4-(4-methyl-benzyl)-piperidine-1-ylmethyl]-indan-1,5-diol (664 mg, 1.81 mmol, 99%) was afforded as a white amorphous foam, (1:1) mixture of diastereoisomers, MS m/e=368.2 (M+H+).

Workup

  1. customAfter removal of the catalyst and evaporation of the solvent the title compound (1RS,2RS)

Sources & evidence

ORD record
ord-f8fa20acabfd4b83826309f5c4b3e028
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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