Borane;tetrahydrofuran → HCID 57285352, compound

To a stirred solution of 1.47 g of the (2S)-2-(t-butylthio)propanoic acid in 22 mL of THF at 0° C. was added dropwise 22 mL of 1M borane/THF over a period of 15 min. Stirring was continued at room temperature for 3 h. The reaction was quenched by dropwise addition of cold water. The mixture was extracted with ether. The organic layer was washed with saturated NaHCO3, saturated NaCl solution and dried over Na2SO4. The solvent was evaporated under vacuum and the residue was purified by flash chromatography (10% EtOAc in hexane) to give 1.10 g of (2S)-2-(tert-butylthio)-1-propanol as an oil at 82% yield. Characteristic analytical data are as follows: 1H NMR (300 MHz, CDCl3) δ3.61 (ddd, J=5, 9, 11 Hz, 1H), 3.33 (ddd, J=4, 8, 11 Hz, 1H), 2.89 (m, 1H), 2.31 (dd, J= 4, 9 Hz, 1H, OH), 1.36 (s, 9H), 1.30 (d, J=7 Hz, 3H); [α]D25 -10.3° (c=2.04, MeOH).

1. customThe reaction was quenched by dropwise addition of cold water
2. extractionThe mixture was extracted with ether
3. washThe organic layer was washed with saturated NaHCO3, saturated NaCl solution
4. dry with materialdried over Na2SO4
5. customThe solvent was evaporated under vacuum
6. customthe residue was purified by flash chromatography (10% EtOAc in hexane)

ORD record

ord-1ed0579a0b644e5db8db966d30cf488b

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05455262