Tetrafluoroborate → 2-(4-Methoxybenzenesulfonylmethyl)pentanoic acid

HRID 650712Notes

Reaction equation

HRID 650712 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](/[CH:12]=[C:13](\[CH2:17][CH2:18][CH3:19])/[C:14]([OH:16])=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.F[B-](F)(F)F.[H][H]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH:13]([CH2:17][CH2:18][CH3:19])[C:14]([OH:16])=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 26255TetrafluoroborateHCID 11108850(E)-3-(4-Methoxybenzenesulfonyl)-2-propylacrylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 109460732-(4-Methoxybenzenesulfonylmethyl)pentanoic acidYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-3-(4-Methoxybenzenesulfonyl)-2-propylacrylic acid (1.0 g, 3.52 mmol) was dissolved in degassed methanol (15 ml) and [(S,S)-MeDuPHOS Rh (COD)]BF4 (22 mg, 3.52×10−2 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 1035 kPa (150 psi) for 2 hour at room temperature. The methanol was removed under reduced pressure to give the title compound (1.0 g, 99% yield). E.e. was determined by chiral HPLC to be 96% [Chirocel OD; 20% IPA-80% heptane; 1 ml/min; 254 nm; major enantiomer Rf 10.91 min., minor enantiomer Rf 9.71 min.]

Workup

  1. customThe methanol was removed under reduced pressure

Sources & evidence

ORD record
ord-c508480b953f44248c3d2617d6562525
Source dataset
uspto-grants-2001_08
Patent number
US06274758B1

Reaction notes

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