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

HRID 1931813

反応式

HRID 1931813 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 251438113-(2,3-Difluorophenyl)-3-fluoropyrrolidine収率 19.3%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5c37fa550b25455f978fc3d3ea5c2e6a
出典データセット
uspto-grants-2012_05
特許番号
US08188301B2

関連ノート

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