Water → trans-{4-(Benzyl-methyl-amino)-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-yl}-methanol

HRID 896553ノート

反応式

HRID 896553 の反応式
C([O:3][C:4]([C@H:6]1[C@H:11]([N:12]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:13])[CH2:10][CH2:9][N:8]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:14]([N:12]([CH3:13])[C@@H:11]1[CH2:10][CH2:9][N:8]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:7][C@H:6]1[CH2:4][OH:3])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69737831HCID 69737831、化合物

生成物 1

HCID 69736397trans-{4-(Benzyl-methyl-amino)-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-yl}-methanol収率 90.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of trans-4-(benzyl-methyl-amino)-1-[2-(4-fluorophenyl)-ethyl]-piperidine-3-carboxylic acid ethyl ester (144 mg, 361 μmol) in tetrahydrofuran (1 mL) was treated with a solution of lithium aluminum hydride (1.0 M in tetrahydrofuran, 723 μL, 723 μmol). The mixture was stirred at room temperature for 2.5 hours, then was treated very slowly with 28 μL of water, followed by 28 μL of 15% aqueous sodium hydroxide, then by 84 μL of water. The mixture was filtered and the solid was washed with ether. The filtrate and washes were combined and concentrated under vacuum to provide a white solid (116 mg, 90%). 1H NMR (300 MHz, CDCl3) δ7.34 (m, 5H), 7.15 (m, 2H), 6.98 (t, J=9 Hz, 2H), 6.26 (bs, 1H), 3.78 (d, J=13 Hz, 1H), 3.60 (m, 2H), 3.50 (m, 1H), 3.10 (m, 1H), 2.87 (m, 1H), 2.78 (m, 2H), 2.54 (m, 2H), 2.28 (s, 3H), 2.20 (m, 1H), 1.88 (m, 2H), 1.75 (m, 1H), 1.58 (m, 1H). Mass spec (ES+) m/z 357.3 (M+H+).

後処理

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with ether
  3. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-7f094ab882434a29a14b18d9818ba24c
出典データセット
uspto-grants-2005_07
特許番号
US06919356B2

反応ノート

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