1-[2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-1-yl]-2-benzyloxy-ethanone → (S)-1-(2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)-2-hydroxyethanone

HRID 1423120Notes

Reaction equation

HRID 1423120 reaction equation
[CH2:1]([CH:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[C:28](=[O:38])[CH2:29][O:30]CC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[C:28](=[O:38])[CH2:29][OH:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 672923701-[2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-1-yl]-2-benzyloxy-ethanone

Product 1

HCID 23627687(S)-1-(2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)-2-hydroxyethanoneYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate 1-[2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-1-yl]-2-benzyloxy-ethanone (60 mg, 0.12 mmol) was dissolved in MeOH (20 mL), purged with a stream of nitrogen, treated with 20% Pd/C (140 mg, 50% water content) and hydrogenated under 40 psi pressure of hydrogen for 4 h. The crude reaction mixture was then purged with nitrogen, filtered, evaporated, and purified by silica gel flash chromatography with 40% then 75% EtOAc/hexane as eluant to afford the title compound as an oil (9 mg, 18%). LC/MS (Method A) 6.55 min, [M+1]+ 425.

Workup

  1. custompurged with a stream of nitrogen
  2. additiontreated with 20% Pd/C (140 mg, 50% water content) and hydrogenated under 40 psi pressure of hydrogen for 4 h
  3. customThe crude reaction mixture
  4. customwas then purged with nitrogen
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by silica gel flash chromatography with 40%

Sources & evidence

ORD record
ord-c6fc4315d5cf4056955357bc70d56f7e
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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