HCID 22628386, compound → HCID 22628329, compound

HRID 278414Notes

Reaction equation

HRID 278414 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:11][N:12]3[CH2:17][CH2:16][C:15]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=4)([OH:18])[CH2:14][CH2:13]3)[CH2:8]2)=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[OH:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][CH:3]=1)[CH2:6][CH:7]([CH2:11][N:12]1[CH2:13][CH2:14][C:15]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)([OH:18])[CH2:16][CH2:17]1)[CH2:8]2

Participants

4

Reactant 1

HCID 22628386HCID 22628386, compound

Product 1

HCID 22628329HCID 22628329, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-(6-Hydroxy-1H-inden-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol (256 mg, 0.732 mmol) and Pd/C 10% (50 mg) in EtOAc (15 ml) was stirred vigorously under a hydrogen atmosphere for 24 hr at RT. Removal of the catalyst and evaporation of the solvent afforded (RS)-1-(5-hydroxy-indan-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol as a colourless oil (235 mg, 0.667 mmol, 91%), MS m/e=352.2 (M+H+).

Workup

  1. customRemoval of the catalyst and evaporation of the solvent

Sources & evidence

ORD record
ord-498fcb5a70634071b993b373c04dcb8f
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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