Water → HCID 21902101, compound

HRID 2110313Notes

Reaction equation

HRID 2110313 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-5ee980732f084ed1859e0de7413982b8
Source dataset
uspto-grants-2009_04
Patent number
US07517892B2

Reaction notes

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