(Dimethyl sulfide)trihydroboron → HCID 66577224, compound

HRID 1512653Notes

Reaction equation

HRID 1512653 reaction equation
CSC.B.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:16][N:15]=[C:14]([CH3:17])[C:13]=2[C:18](=[O:29])[CH2:19][O:20][C@@H:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])=[CH:8][CH:7]=1>C1COCC1>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:16][N:15]=[C:14]([CH3:17])[C:13]=2[C@H:18]([OH:29])[CH2:19][O:20][C@@H:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 66577479HCID 66577479, compound

Product 1

HCID 66577224HCID 66577224, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

The (S)-Corey-Bakshi-Shibata catalyst (0.012 g, 0.04 mmol) was dissolved in THF (2 mL) and cooled to 0° C. Borane dimethyl sulfide complex (2.0 M in THF, 0.387 mL, 0.77 mmol) was slowly added, followed by 1-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-2-((R)-1-phenyl-ethoxy)-ethanone (0.172 g, 0.43 mmol) in THF (3.3 mL) over 15 minutes. After stirring for 55 minutes the reaction was submitted to standard aqueous workup to afford the title compound.

Sources & evidence

ORD record
ord-49368018284b4b9cb990cb9d58873ee5
Source dataset
uspto-grants-2012_07
Patent number
US08217066B2

Reaction notes

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