2-Methoxyphenyl-4-[3-(cyclohexanecarbonyl)-3-(phenyl)propyl]piperazine → 1-(2-Methoxyphenyl)-4-[4-(cyclohexyl)-4-(hydroxy)-3-(phenyl)butyl]piperazine

HRID 1789995Notes

Reaction equation

[CH:1]1([C:7](=[O:31])[CH:8]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])[CH2:13][CH2:12]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl.C1(C)C=CC=CC=1>[CH:1]1([CH:7]([OH:31])[CH:8]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])[CH2:15][CH2:16]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: -78 °C

Procedure

Into a solution of 1.21 g of Compound 5d in 60 ml of dichloromethane at −78° C., was dropped 11.5 ml of 1 M solution of diisobutylaluminum hydride (DIBAL-H) in toluene. The mixture was stirred at −78° C. for 1 h, quenched at 40° C. with a saturated aqueous solution of NH4Cl and extracted with chloroform. The collected organic layers were washed with water, dried (Na2SO4) and the solvent was evaporated under vacuum. The crude was purified by flash chromatography eluting with petroleum ether-EtOAc-2 N ammonia in methanol 30:70:2 to give 1.06 g (80%) of the title compound.

Workup

customquenched at 40° C. with a saturated aqueous solution of NH4Cl
extractionextracted with chloroform
washThe collected organic layers were washed with water
dry with materialdried (Na2SO4)
customthe solvent was evaporated under vacuum
customThe crude was purified by flash chromatography
washeluting with petroleum ether-EtOAc-2 N ammonia in methanol 30:70:2

Sources & evidence

ORD record: ord-a2c6d18735294db9a4cec801c19b3d02
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071197B2

Reaction notes

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