Water → [((1R,2R)-1-(3-chlorophenyl)-2-{2-[(phenylmethyl)oxy]ethyl}cyclopropyl)methyl]amine

HRID 2099296ノート

反応式

HRID 2099296 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]2([C:21]#[N:22])[CH2:10][C@@H:9]2[CH2:11][CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]2([CH2:21][NH2:22])[CH2:10][C@@H:9]2[CH2:11][CH2:12][O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 57794790(1R,2R)-1-(3-chlorophenyl)-2-{2-[(phenylmethyl)oxy]ethyl}cyclopropanecarbonitrile

生成物 1

HCID 57794800[((1R,2R)-1-(3-chlorophenyl)-2-{2-[(phenylmethyl)oxy]ethyl}cyclopropyl)methyl]amine

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A solution of (1R,2R)-1-(3-chlorophenyl)-2-{2-[(phenylmethyl)oxy]ethyl}cyclopropanecarbonitrile (1.26 g, 4.0 mmol) in diethyl ether at 0° C. was treated with 2 equivalents of LAH (1M in diethyl ether). After 1.5 hours at 0° C., water was added dropwise until no further evolution of gas was observed. The aluminum salts were filtered off and washed with diethyl ether. Evaporation of the diethyl ether afforded the title compound. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 0.5 (dd, J=5.9, 4.8 Hz, 1H) 1.0 (dd, J=8.9, 4.7 Hz, 1H) 1.2 (m, 1H) 1.4 (s, 2H) 1.8 (m, 2H) 2.9 (m, 2H) 3.6 (m, 2H) 4.6 (s, 2H) 7.2 (m, 3H) 7.3 (m, 2H) 7.4 (m, 4H).

後処理

  1. filtrationThe aluminum salts were filtered off
  2. washwashed with diethyl ether
  3. customEvaporation of the diethyl ether

出典と根拠

ORDレコード
ord-e1c5c066330542c1901da54c8e517671
出典データセット
uspto-grants-2009_08
特許番号
US07569579B2

反応ノート

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