Toluene → 2alpha-[[1-[3,5-Bis(trifluoromethyl)phenyl]vinyl]oxy]3alpha-(4-fluorophenyl)-4-benzylmorpholine

HRID 442646노트

반응식

HRID 442646 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][C@@H:10]([O:14][CH2:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)[C@@H:9]1[C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCC[CH2:38]1.C1(C)C=CC=CC=1>C[C-]1C=CC=C1.[C-]1(C)C=CC=C1.[Ti+2].C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([O:14][C:15]([C:16]2[CH:17]=[C:18]([C:26]([F:27])([F:28])[F:29])[CH:19]=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:21]=2)=[CH2:38])[C@@H:9]1[C:30]1[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 1140TolueneHCID 8028TetrahydrofuranHCID 213088524-benzyl-2-(R)-[3,5-bis(trifluoromethyl)benzyloxy]-3-(S)-(4-fluorophenyl)morpholine

생성물 1

HCID 113529882alpha-[[1-[3,5-Bis(trifluoromethyl)phenyl]vinyl]oxy]3alpha-(4-fluorophenyl)-4-benzylmorpholine수율 69%

시약·촉매·용매 2

HCID 129651941Dimethyl titanocene촉매HCID 6344Dichloromethane용매

실험 절차

A solution of 4-benzyl-2-(R)-[3,5-bis(trifluoromethyl)benzyloxy]-3-(S)-(4-fluorophenyl)morpholine (2.50 g, 4.9 mmol) and dimethyl titanocene (2.50 g, 12.0 mmol) in 35 ml of a 1:1 v/v tetrahydrofuran:toluene mixture is stirred in an oil bath at 80° C. for sixteen hours. The reaction mixture is cooled and centrated in vacuo. Flash chromatography on 150 grams of silica gel using 3:1 v/v hexanes:methylene chloride as the eluant affords 1.71 grams (69%) of the title compound as a solid. If desired, an anlytical sample may be obtained by recrystallization from isopropanol.

후처리

  1. temperatureThe reaction mixture is cooled

출처 및 근거

ORD 기록
ord-18da858cdd6943a387936120427b8f3f
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891875

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