Ethyl Acetate → 2-Methylpentane

A solution of tetrabutylammonium fluoride (1M in THF) (8.63 mL, 8.63 mmol) was added in one portion to a stirred solution of (S)-2-(tert-butyldimethylsilyloxy)-3-methoxy-N-(5-methylpyridin-2-yl)propanamide C4d (1.4 g, 4.31 mmol) in THF (20 mL). The resulting solution was stirred at ambient temperature for 4 hours. The reaction mixture was concentrated, diluted with EtOAc (50 mL) and washed sequentially with water (20 mL) and saturated brine (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product as an oil. Trituration with 1:1 isohexane:EtOAc afforded (S)-2-hydroxy-3-methoxy-N-(5-methylpyridin-2-yl)propanamide (340 mg). The residue was purified by flash silica chromatography with EtOAc to afford a second batch of (S)-2-hydroxy-3-methoxy-N-(5-methylpyridin-2-yl)propanamide (220 mg).

1. concentrationThe reaction mixture was concentrated
2. additiondiluted with EtOAc (50 mL)
3. washwashed sequentially with water (20 mL) and saturated brine (20 mL)
4. dry with materialThe organic layer was dried over MgSO4
5. filtrationfiltered
6. customevaporated
7. customto afford crude product as an oil

ORD record

ord-d7bad640a6ce49d79e1da3d7607aff6d

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143263B2