Potassium ethanethioate → tert-Butyl (2R,4S)-4-(acetylsulfanyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 1941603노트

반응식

HRID 1941603 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11](OS(C)(=O)=O)[CH2:10][C@@H:9]1[CH2:18][OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:20]([O-:23])(=[S:22])[CH3:21].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:20]([S:22][C@@H:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C@@H:9]([CH2:18][OH:19])[CH2:10]1)(=[O:23])[CH3:21]

참가 물질

5

반응물 2

HCID 23670855Potassium ethanethioateHCID 53830029(2R,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol

생성물 1

HCID 57080293tert-Butyl (2R,4S)-4-(acetylsulfanyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

(2R,4R)-1-t-Butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol (i.e., a substrate) and potassium thioacetate (KSAc) are dissolved in dimethylformamide (DMF), and the mixture is stirred. The conditions for this reaction are shown in Table 1, Step A-5. The reaction mixture is diluted with ethyl acetate, and ice water is added. The organic layer is taken, successively washed with aqueous sodium hydroxide, hydrochloric acid, water and saturated brine, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by silica gel chromatography to give (2R,4S)-4-acetylthio-1-t-butoxycarbonylpyrrolidine-2-methanol.

후처리

  1. additionis added
  2. washsuccessively washed with aqueous sodium hydroxide, hydrochloric acid, water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-9a16b74a51654fa0b91adcb9a0b61f85
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05703243

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