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

HRID 16331

反応式

HRID 16331 の反応式
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

参加物

7

反応物 4

HCID 3283Diethyl Ether2 回HCID 146262(2S)-2-MethyloxiraneHCID 23665649Lithium perchlorateHCID 68719033(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamine

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A diethyl ether 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 diethyl ether suspension (1 mL) of lithium perchlorate (750 mg). This reaction solution was stirred in nitrogen atmosphere at room temperature overnight. To this reaction solution, methylene chloride and iced-water were added. The organic layer was separated, and the water 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 (eluting solvent; ethyl acetate:heptane=9:1 to 4:1) to give 172 mg of the title compound. The physical property values of this compound were as follows:

後処理

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

出典と根拠

ORDレコード
ord-22c09812ab944d188fe4d4c249879f9f
出典データセット
uspto-grants-2010_06
特許番号
US07737141B2

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