Lawesson's reagent → tert-Butyl (S)-5-thioxo-2-pyrrolidinecarboxylate

HRID 1737849ノート

反応式

HRID 1737849 の反応式
[C:1]([O:5][C:6]([C@H:8]1[NH:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1C=CC=CC=1>[C:1]([O:5][C:6]([C@H:8]1[NH:12][C:11](=[S:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 10888648tert-Butyl 5-oxo-L-prolinate

生成物 1

HCID 14416882tert-Butyl (S)-5-thioxo-2-pyrrolidinecarboxylate収率 158.1%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To a solution of (S)-pyrrolidin-2-one-5-carboxylic acid t-butyl ester (2.04 g, 11.01 mmol) in benzene was added Lawesson's Reagent (2.22 g, 5.50 mmol). The reaction mixture was heated at reflux overnight, concentrated under vacuum, and purified by column chromatography on silica gel (5% MeOH/CHCl3) to provide (S)-pyrrolidin-2-thione-5-carboxylic acid t-butyl ester (1.75 g, 79%) as a tan solid. 1H NMR (CDCl3) δ 1.49 (s, 9H), 2.30 (m, 1H), 2.53 (m, 1H), 2.85-3.04 (m, 2H), 4.42 (t, 1H, J=7.7 Hz), 7.88 (bs, 1H). MS calcd for C9H15NO2S+H 202, found 202.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under vacuum
  4. custompurified by column chromatography on silica gel (5% MeOH/CHCl3)

出典と根拠

ORDレコード
ord-1f8d4caff67d487f8eeaae2a16546edb
出典データセット
uspto-grants-1999_10
特許番号
US05962487

反応ノート

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