Diethyl Ether → (S)-1-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]propan-2-ol

HRID 16359

반응식

HRID 16359 반응식
C(OCC)C.[CH2:6]1[O:9][C@H:7]1[CH3:8].[Si:10]([O:27][C@H:28]([CH3:40])[C@H:29]([NH2:39])[C:30]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl([O-])(=O)(=O)=O.[Li+]>O.C(Cl)Cl>[Si:10]([O:27][C@H:28]([CH3:40])[C@H:29]([NH:39][CH2:6][C@@H:7]([OH:9])[CH3:8])[C:30]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=1)([C:23]([CH3:24])([CH3:25])[CH3:26])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

참가 물질

7

반응물 4

HCID 3283Diethyl Ether2회HCID 146262(2S)-2-MethyloxiraneHCID 23665649Lithium perchlorateHCID 68719033(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamine

생성물 1

HCID 68718733(S)-1-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]propan-2-ol

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A diethylether solution (1 mL) of (S)-(−)-propylene oxide (0.1 mL) and (1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamine (212 mg) was added to a diethylether suspension (1 mL) of lithium perchlorate (750 mg). The resulting reaction solution was stirred in nitrogen atmosphere at room temperature overnight, and then methylene chloride and iced-water were added thereto. The resulting mixture was stirred. The organic layer was separated, and the water layer was re-extracted with methylene chloride. The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (heptane: ethyl acetate=9:1 to 4:1) to give 172 mg of the title compound. The physical property values of this compound were as follows:

후처리

  1. customThe resulting reaction solution
  2. stirringThe resulting mixture was stirred
  3. customThe organic layer was separated
  4. extractionthe water layer was re-extracted with methylene chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (heptane: ethyl acetate=9:1 to 4:1)

출처 및 근거

ORD 기록
ord-54f9861583f942bdb53e64fbb12c2a63
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737141B2

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