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

HRID 720046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 720046
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1-[1-(2-Methoxy-phenyl)-cylobutyl]-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 δ 3.09 singlet for the starting material was absent.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-4b9767c162384cbb84031dfdf1deae69
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132551B2

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