Water → HCID 21902111, compound

HRID 2110316Notes

Reaction equation

HRID 2110316 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:33]=[CH:32][C:6]([O:7][CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][C:16]([C:18]3([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)[CH2:21][CH2:20][CH2:19]3)=[O:17])[CH2:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+].O>CO>[F:34][C:2]([F:1])([F:35])[C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH:16]([C:18]3([C:22]4[CH:23]=[CH:24][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:26][CH:27]=4)[CH2:21][CH2:20][CH2:19]3)[OH:17])[CH2:10]2)=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21901987HCID 21901987, compound

Product 1

HCID 21902111HCID 21902111, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[3-(4-Trifluoromethyl-phenoxymethyl)-piperidin-1-yl]-1-[1-(4-trifluoromethyl-phenyl)-cyclobutyl]-ethanone (30 mg) was dissolved in 3 mL of dry methanol and solid sodium borohydride (10 equiv.) was added in portions. Water (10 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 2-[3-(4-Trifluoromethyl-phenoxymethyl)-piperidin-1-yl]-1-[1-(4-trifluoromethyl-phenyl)-cyclobutyl]-ethanol (21 mg, 67%). Data for this mixture of diastereomeric amino alcohols: MS 502 (M+1); 1H NMR (300 MHz, CDCl3): δ 7.5-7.6 (m, 4H), 7.29-7.35 (m, 2H), 6.89-6.96 (overlapping doublets, total 2 H), 3.8-4.0 (m, 4H, 1 of which is exchanged upon exposure to D2O), 1.1-3.1 9 (various overlapping multiplets totaling 17 H); 13C NMR (75 MHz, CDCl3): δ 207 peak in starting ketone is absent. Most peaks are doubled (adjacent equal intensity peaks) due to diastereoisomerism: δ 161.7, 151.0, 128.6 & 128.5, 128.0 & 127.8, 127.15 & 127.10, 126.45, 124.91 & 124.87, 123.30, 122.86, 114.63, 71.2 & 71.1, 59.7 & 59.5, 58.99 & 58.97, 55.96, 49.31 & 49.28, 36.8 & 36.6, 31.0, 29.5 & 29.4, 27.33 & 27.26, 25.24 & 25.03, 16.42.

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-f59457985c784512b736a2bd25c3b7c6
Source dataset
uspto-grants-2009_04
Patent number
US07517892B2

Reaction notes

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