p-Bromobenzenesulfonyl chloride → (R)-(1-(4-bromophenylsulfonyl)pyrrolidin-2-yl)methanol

HRID 39156

반응식

HRID 39156 반응식
C([O-])(O)=O.[Na+].[NH:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[CH2:11][OH:12].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>C(Cl)Cl>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([N:6]2[CH2:10][CH2:9][CH2:8][C@@H:7]2[CH2:11][OH:12])(=[O:22])=[O:21])=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 2724541Prolinol, (R)-

생성물 1

HCID 59166148(R)-(1-(4-bromophenylsulfonyl)pyrrolidin-2-yl)methanol수율 90.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
20 °C

실험 절차

To a mixture of sat aq. NaHCO3 (44 g, 0.53 mol), CH2Cl2 (400 mL) and (R)-pyrolidin-2-yl-methanol (53 g, 0.53 mol) was added 4-bromo-benzenesulfonyl chloride (130 g, 0.50 mol) in CH2Cl2 (100 mL). The reaction was stirred at 20° C. overnight. The organic phase was separated and dried over Na2SO4. Evaporation of the solvent under reduced pressure provided (R)-[1-(4-bromo-benzenesulfonyl)-pyrrolidin-2-yl]-methanol (145 g, crude), which was used in the next step without further purification. 1H NMR (CDCl3, 300 MHz) δ 7.66-7.73 (m, 4H), 3.59-3.71 (m, 3H), 3.43-3.51 (m, 1H), 3.18-3.26 (m, 1H), 1.680-1.88 (m, 3H), 1.45-1.53 (m, 1H).

후처리

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. customEvaporation of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-38557618aaf74f3e8bc27bdb1e132c11
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524767B2

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