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

HRID 2099296노트

반응식

HRID 2099296 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-e1c5c066330542c1901da54c8e517671
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569579B2

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