Sodium borohydride → 1,1,1,3,3,3-Hexafluoro-2-(2-(hydroxymethyl)thiazol-5-yl)propan-2-ol

To a stirring solution of 5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)thiazole-2-carbaldehyde (1.791 mmol, 500 mg) in methanol (4 mL) was added sodium borohydride (5.37 mmol, 203 mg). The mixture was stirred at room temperature for 90 minutes before concentrating under reduced pressure. The resulting residue was dissolved in dichloromethane (2 mL)/methanol (0.5 mL) and filtered through a plug of silica, washing with 20% methanol/80% dichloromethane. The filtrate was concentrated under reduced pressure to afford the title compound (150 mg). MS (ESI) m/z 280.0 [M−H]

1. concentrationbefore concentrating under reduced pressure
2. dissolutionThe resulting residue was dissolved in dichloromethane (2 mL)/methanol (0.5 mL)
3. filtrationfiltered through a plug of silica
4. washwashing with 20% methanol/80% dichloromethane
5. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-5027a6403c084e56aa16def27e4a7e31

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08357679B2