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

HRID 1436111Notes

Reaction equation

HRID 1436111 reaction equation
[CH2:1]1[O:4][C@H:2]1[CH3:3].[Si:5]([O:22][C@H:23]([CH3:35])[C@H:24]([NH2:34])[C:25]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[C:27]([F:33])[CH:26]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl([O-])(=O)(=O)=O.[Li+].C(Cl)Cl>C(OCC)C>[Si:5]([O:22][C@H:23]([CH3:35])[C@H:24]([NH:34][CH2:1][C@@H:2]([OH:4])[CH3:3])[C:25]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[C:27]([F:33])[CH:26]=1)([C:18]([CH3:19])([CH3:20])[CH3:21])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 146262(2S)-2-MethyloxiraneHCID 23665649Lithium perchlorateHCID 68719033(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamine

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of (S)-(−)-propylene oxide (0.1 ml) and (1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamine (212 mg) in diethyl ether (1 ml) was added to a suspension of lithium perchlorate (750 mg) in diethyl ether (1 ml), and the reaction solution was stirred in a nitrogen atmosphere at room temperature overnight. Methylene chloride and ice water were added to the reaction solution. After stirring the reaction solution, the organic layer was separated. The aqueous layer was subjected to extraction with methylene chloride again. The organic layers were combined and dried over anhydrous magnesium sulfate, and then the solvent was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:heptane=9:1 to 4:1) to obtain 172 mg of the title compound.

Workup

  1. stirringAfter stirring the reaction solution
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was subjected to extraction with methylene chloride again
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:heptane=9:1 to 4:1)

Sources & evidence

ORD record
ord-2c52d54976b046f6a014fd57bb4c70b2
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

Loading…