Water → 1-[1-(2-Methoxy-phenyl)-cyclobutyl]-2-[3-(4-trifluoromethyl-phenoxymethyl)-piperidin-1-yl]-ethanol

HRID 1160361Notes

Reaction equation

HRID 1160361 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:13](=[O:33])[CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)[CH2:16]2)[CH2:12][CH2:11][CH2:10]1.[BH4-].[Na+].O>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([CH:13]([OH:33])[CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][CH:24]=3)[CH2:16]2)[CH2:10][CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 219019461-[1-(2-Methoxy-phenyl)-cyclobutyl]-2-[3-(4-trifluoromethyl-phenoxymethyl)-piperidin-1-yl]-ethanone

Product 1

HCID 219019431-[1-(2-Methoxy-phenyl)-cyclobutyl]-2-[3-(4-trifluoromethyl-phenoxymethyl)-piperidin-1-yl]-ethanolYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[1-(2-Methoxy-phenyl)-cyclobutyl]-2-[3-(4-trifluoromethyl-phenoxymethyl)-piperidin-1-yl]-ethanone (15 mg) was dissolved in 2 mL of dry methanol and solid sodium borohydride (10 equiv.) was added in portions. Water (5 mL) was added and the mixture was extracted with ether and the ether extracts were concentrated in vacuo and purified on silica gel to give the desired 1-[1-(2-methoxy-phenyl)-cyclobutyl]-2-[3-(4-trifluoromethyl-phenoxymethyl)-piperidin-1-yl]-ethanol (9 mg, 60%). Data for this mixture of diastereomeric amino alcohols: MS 464 (M+1); 1H NMR (300 MHz, CDCl3) partial: δ 6.8-7.6 (m, 8H), 3.85-3.95 (m, 2H, methylene adjacent to aryl ether), the 63.09 singlet for the starting material was absent.

Workup

  1. extractionthe mixture was extracted with ether
  2. concentrationthe ether extracts were concentrated in vacuo
  3. custompurified on silica gel

Sources & evidence

ORD record
ord-d38e3a7725db43f6aac05b5666086ec2
Source dataset
uspto-grants-2010_10
Patent number
US07816375B2

Reaction notes

Loading…