Methanesulfonyl chloride → (2R,3S)-3-Hydroxy-2-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 449827노트

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HRID 449827 반응식
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:3]1[CH2:14][OH:15].C([Sn](CCCC)=O)CCC.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C1(C)C=CC=CC=1>[C:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][C@H:2]([OH:1])[C@H:3]1[CH2:14][O:15][S:27]([CH3:26])(=[O:29])=[O:28])=[O:8])([CH3:11])([CH3:12])[CH3:13]

참가 물질

5

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 61221Dibutyltin oxideHCID 10910976tert-butyl (2R,3S)-3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

생성물 1

HCID 58149374(2R,3S)-3-Hydroxy-2-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester수율 96%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
130 °C

실험 절차

A suspension of (2R,3S)-tert-butyl 3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate (5.04 g, 23.20 mmol) and dibutyloxostannane (7.07 g, 27.84 mmol) in toluene (50 mL) is refluxed in a 130° C. oil bath for 2 h. The mixture is cooled to 0° C. in an ice bath for 30 min and treated with methanesulfonyl chloride (2.15 mL, 27.84 mmol) at once. The reaction is stirred for 30 min at 0° C. and then the mixture allowed to gradually warm to ambient temperature overnight. The solution is concentrated and the resulting residue purified by medium pressure liquid chromatography, eluting with ethyl acetate:hexane (8:2). Fractions containing pure product are combined and concentrated to give 6.14 g (96%) of dense oil as the title compound. LC-ES/MS m/z 318.2 [M+Na]+, TR=2.34 min.

후처리

  1. temperatureThe mixture is cooled to 0° C. in an ice bath for 30 min
  2. temperatureto gradually warm to ambient temperature overnight
  3. concentrationThe solution is concentrated
  4. customthe resulting residue purified by medium pressure liquid chromatography
  5. washeluting with ethyl acetate:hexane (8:2)
  6. additionFractions containing pure product
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4e2e5afd2577434988251baf9d8ff4e9
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486943B2

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