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

HRID 1436115Notes

Reaction equation

HRID 1436115 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-7092199bd42b43baba168944743a1fb7
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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