Methanol → 3-(2,3-Difluorophenyl)-3-fluoropyrrolidine

HRID 1931813노트

반응식

HRID 1931813 반응식
C([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=2[F:21])([F:13])[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C.CO>ClCCCl>[F:21][C:15]1[C:16]([F:20])=[CH:17][CH:18]=[CH:19][C:14]=1[C:10]1([F:13])[CH2:11][CH2:12][NH:8][CH2:9]1

참가 물질

5

반응물 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 685171501-Benzyl-3-(2,3-difluorophenyl)-3-fluoropyrrolidine

생성물 1

HCID 251438113-(2,3-Difluorophenyl)-3-fluoropyrrolidine수율 19.3%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of 1-benzyl-3-(2,3-difluorophenyl)-3-fluoropyrrolidine (1.6 g, 5.5 mmol) in dry 1,2-dichloroethane (10 mL) under nitrogen was added 1-chloroethylchloroformate (600 μl, 5.5 mmol). The mixture was stirred at ambient temperature for 7 h after which methanol was added and the mixture was evaporated. Methanol (10 mL) was added and the mixture was heated at reflux for 4 h. The mixture was evaporated and purified by column chromatography on silica gel (ethyl acetate/methanol, 1:0 to 1:1) to give the title compound (214 mg). The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 136° C.; MS m/z (relative intensity, 70 eV) 201 (M+, 35), 151 (bp), 158 (69), 138 (45), 133 (42).

후처리

  1. additionwas added
  2. customthe mixture was evaporated
  3. additionMethanol (10 mL) was added
  4. temperaturethe mixture was heated
  5. temperatureat reflux for 4 h
  6. customThe mixture was evaporated
  7. custompurified by column chromatography on silica gel (ethyl acetate/methanol, 1:0 to 1:1)

출처 및 근거

ORD 기록
ord-5c37fa550b25455f978fc3d3ea5c2e6a
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188301B2

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