3-(Piperidine-1-sulfonyl)benzoic acid → (3-(Piperidin-1-ylsulfonyl)phenyl)methanol

HRID 1967557Notes

Reaction equation

[N:1]1([S:7]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13](O)=[O:14])(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>C1COCC1.O>[N:1]1([S:7]([C:10]2[CH:11]=[C:12]([CH2:13][OH:14])[CH:16]=[CH:17][CH:18]=2)(=[O:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

3-(Piperidin-1-ylsulfonyl)benzoic acid (7.00 g) was dissolved in THF (70 mL), and at 0° C., N,N′-carbodiimidazole (6.32 g) was added thereto and stirred at 0° C. for 4 hours. A solution prepared by dissolving sodium borohydride (1.97 g) in water (10 mL) was dropwise added to the reaction liquid, and then stirred at 0° C. for 1 hour. Water was added thereto, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 100%, gradient) to give the entitled compound (7.01 g, 100%) as a colorless oil.

Workup

customA solution prepared
additionwas dropwise added to the reaction liquid
stirringstirred at 0° C. for 1 hour
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried with sodium sulfate
customThe drying agent was removed through filtration
customthe solvent was evaporated off under reduced pressure
customThe residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 100%, gradient)

Sources & evidence

ORD record: ord-7f37e1f358a04d139700ae9a0b0c8d92
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420823B2

Reaction notes

Loading…