Water → HCID 21902101, compound

HRID 1593117Notes

Reaction equation

HRID 1593117 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-3f170c620b8643d18acfb7d111faa2e9
Source dataset
uspto-grants-2007_11
Patent number
US07294637B2

Reaction notes

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