Tetrabutylammonium Fluoride → HCID 59279518, compound

Tetrabutylammonium fluoride (1M in THF) (2071 μl, 2.07 mmol) was added to (S)-methyl 2-(tert-butyldiphenylsilyloxy)-4-(methylsulfonyl)butanoate (Intermediate AA3) (450 mg, 1.04 mmol) in THF (3106 μl) under nitrogen. The resulting mixture was stirred at ambient temperature for 2 hours. The reaction mixture was quenched with saturated NH4Cl (10 mL), extracted with Et2O (3×15 mL). The combined organic layers were back washed with water (10 mL), dried (MgSO4) and evaporated. The crude product was purified by flash silica chromatography, eluting with 0 to 100% ethyl acetate in isohexane to afford the product (120 mg, 59%). 1H NMR (400 MHz, CDCl3) δ 2.10-2.20 (1H, m), 2.38-2.46 (1H, m), 2.94 (4H, m), 3.10-3.24 (2H, m), 3.84 (3H, s), 4.34 (1H, q), 7.26 (3H, s).

1. customThe reaction mixture was quenched with saturated NH4Cl (10 mL)
2. extractionextracted with Et2O (3×15 mL)
3. washThe combined organic layers were back washed with water (10 mL)
4. dry with materialdried (MgSO4)
5. customevaporated
6. customThe crude product was purified by flash silica chromatography
7. washeluting with 0 to 100% ethyl acetate in isohexane

ORD record

ord-9112af410c0943949d87d22f4d38828f

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143263B2