Tetrafluoroborate → HCID 21713174, compound

HRID 650713Notes

Reaction equation

HRID 650713 reaction equation
[CH2:1](/[C:4](=[CH:8]\[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10])/[C:5]([OH:7])=[O:6])[CH2:2][CH3:3].F[B-](F)(F)F.[H][H]>CO>[C:12]1([S:9]([CH2:8][CH:4]([CH2:1][CH2:2][CH3:3])[C:5]([OH:7])=[O:6])(=[O:11])=[O:10])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 26255TetrafluoroborateHCID 21713168HCID 21713168, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21713174HCID 21713174, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-2-Propyl-3-phenylsulfonylacrylic acid (0.3 g, 1.18 mmol) was dissolved in degassed methanol (15 ml) and [(S,S)-EtDuPHOS Rh (COD)]BF4 (8 mg, 1.18×10−2 mmol) was added under a stream of nitrogen. This solution was injected into the pressure vessel under nitrogen, and then the bomb was charged with hydrogen. The mixture was hydrogenated at 2070 kPa (300 psi) for 3 hour at room temperature. The methanol was removed under reduced pressure to give the title compound (0.31 g, 100% yield). E.e. was determined by chiral HPLC to be 92% e.e. [Chiropak AD; 5% ethanol-95% heptane; 1 ml/min; 254 nm; major enantiomer Rf 18.46 min., minor enantiomer Rf 15.22 min.]

Workup

  1. customThe methanol was removed under reduced pressure

Sources & evidence

ORD record
ord-c6316d96986a4f16a0594c5dc77950a7
Source dataset
uspto-grants-2001_08
Patent number
US06274758B1

Reaction notes

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