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

HRID 1357111

반응식

HRID 1357111 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-fcc517176e014f6da14dd1fa6a75060d
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06589978B2

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