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Sulfuric Acid → (3S,4S)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid methyl ester

HRID 1880222
ノート
印刷プレビュー

反応式

HRID 1880222 の反応式
[CH2:1]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C@H:10]([C:20]([OH:22])=[O:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.Cl[CH2:29]Cl.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:29][O:21][C:20]([C@H:10]1[C@@H:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[CH2:12][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9]1)=[O:22]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 46832835(3S,4S)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid

生成物 1

HCID 67530980(3S,4S)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid methyl ester収率 96%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

反応条件

温度
60 °C

実験手順

(3S,4S)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid (7.0 g, 22.0 mmol) were dissolved in methanol (75 mL) and at ambient temperature treated with sulfuric acid 97% (2.4 mL). The reaction mixture was stirred at 60° C. for 18 h. At 0° C. dichloro methane (150 mL) was added followed by aqueous sodium carbonate 10% (150 mL) (final pH 11) under vigorous stirring. The phases were separated. The aqueous phase was washed with dichloro methane, the combined organic phases with water and brine and then dried on sodium sulfate. After filtration and evaporation of the solvent the title product was obtained as a light brown oil (7.0 g, 96%) which was directly used in the next step. ES-MS m/e: 330.8 (M+H+).

後処理

  1. customThe phases were separated
  2. washThe aqueous phase was washed with dichloro methane
  3. dry with materialthe combined organic phases with water and brine and then dried on sodium sulfate
  4. filtrationAfter filtration and evaporation of the solvent the title product

出典と根拠

ORDレコード
ord-6b85b413717349608f4b666021fb194c
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08318759B2

反応ノート

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