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Sodium Sulfate → 2-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]ethanol

HRID 1436115
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HRID 1436115 반응식
[BH4-].[Li+].[Si:3]([O:20][C@H:21]([CH3:39])[C@H:22]([NH:32][CH2:33][C:34](OCC)=[O:35])[C:23]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[C:25]([F:31])[CH:24]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Si:3]([O:20][C@H:21]([CH3:39])[C@H:22]([NH:32][CH2:33][CH2:34][OH:35])[C:23]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[C:25]([F:31])[CH:24]=1)([C:16]([CH3:18])([CH3:19])[CH3:17])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1
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참가 물질

5

반응물 3

HCID 24436Sodium SulfateHCID 4148881Lithium borohydrideHCID 86633283ethyl [(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]acetate

생성물 1

HCID 689073882-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]ethanol수율 70.8%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

Lithium borohydride (20 mg) was added to a solution of ethyl [(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]acetate (158 mg) in THF (3 ml) in a nitrogen atmosphere, and the reaction solution was stirred at room temperature for one day. A saturated sodium sulfate solution was added to the reaction solution, and then the precipitated insoluble matter was removed by filtration through celite. Methanol was added to the filtrate, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1) to obtain 103 mg of the title compound.

후처리

  1. customthe precipitated insoluble matter was removed by filtration through celite
  2. additionMethanol was added to the filtrate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-7092199bd42b43baba168944743a1fb7
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07618960B2

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