Water → HCID 21902101, compound

HRID 720049Notes

Reaction equation

HRID 720049 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:14](=[O:34])[CH2:15][N:16]4[CH2:21][CH2:20][CH2:19][CH:18]([CH2:22][O:23][C:24]5[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=5)[CH2:17]4)[CH2:13][CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[BH4-].[Na+].O>CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH:14]([OH:34])[CH2:15][N:16]4[CH2:21][CH2:20][CH2:19][CH:18]([CH2:22][O:23][C:24]5[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:26][CH:25]=5)[CH2:17]4)[CH2:13][CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21901928HCID 21901928, compound

Product 1

HCID 21902101HCID 21902101, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(1-Benzo[1,3]dioxol-5-yl-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-benzo[1,3]dioxol-5-yl-cyclobutyl)-2-[3-(4-trifluoromethyl-phenoxymethyl)-piperidin-1-yl]-ethanol (10 mg, 66%). Data for this mixture of diastereomeric amino alcohols: MS 478 (M+1); 1H NMR (300 MHz, CDCl3) partial: δ 6.7–7.8 (m, 7H), 3.85–3.95 (m, 2H, methylene adjacent to aryl ether), the δ 3.1 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-3828489a4cc94a818a8a9f24a890b562
Source dataset
uspto-grants-2006_11
Patent number
US07132551B2

Reaction notes

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