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

HRID 449827ノート

反応式

HRID 449827 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4e2e5afd2577434988251baf9d8ff4e9
出典データセット
uspto-grants-2013_07
特許番号
US08486943B2

反応ノート

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