4-Toluenesulfonyl chloride → (2RS,5SR)-5-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

HRID 890253

反応式

HRID 890253 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>ClCCl>[CH3:16][O:15][C:13]([CH:11]1[CH2:10][CH2:9][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[N:12]1[S:30]([C:27]1[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=1)(=[O:32])=[O:31])=[O:14]

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 67257147methyl (2RS,5SR)-5-(4-fluoro-phenyl)-pyrrolidine-2-carboxylate

生成物 1

HCID 69596768(2RS,5SR)-5-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of methyl (2RS,5SR)-5-(4-fluoro-phenyl)-pyrrolidine-2-carboxylate (2.27 g, 10.2 mmol) and triethylamine (2.13 ml, 15.3 mmol) in dichloromethane (60 ml) was added at 0° C. toluene-4-sulfonyl chloride (2.32 g, 12.2 mmol). The mixture was stirred at RT for 16 h, evaporated, dissolved in water (50 ml) and extracted with dichloromethane (2×40 ml). The combined organic layers were washed with water (40 ml), brine (40 ml), dried (MgSO4) and evaporated. The crude product was purified by crystallization from diethyl ether/hexane to give the title compound, off-white solid, m.p. 91° C. and MS: m/e=378.3 (M+H+).

後処理

  1. customevaporated
  2. dissolutiondissolved in water (50 ml)
  3. extractionextracted with dichloromethane (2×40 ml)
  4. washThe combined organic layers were washed with water (40 ml), brine (40 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was purified by crystallization from diethyl ether/hexane

出典と根拠

ORDレコード
ord-7b718a8cb6ec46f0aee5d6b190df76e3
出典データセット
uspto-grants-2006_02
特許番号
US06995182B2

関連ノート

読み込み中…