Methyl iodide → HCID 86700737, compound

Temperature

23 °C

To a cold (0° C.) solution of (2R,3S)-t-Butyl 3-((S)-2,2-dimethyl-1,3-dioxan-4-yl)-2-hydroxypent-4-enoate (0.12 g, 0.40 mmol) in THF (5 mL) was added sodium hydride (20.0 mg, 0.8 mmol) followed by methyl iodide (50.0 μL, 0.80 mmol). The reaction was allowed to stir for 2 h at 23° C. then quenched with saturated ammonium chloride (5 mL). The reaction mixture was extracted with ethyl acetate (3×10 mL). The organic layers were combined, washed with brine and dried over anhydrous sodium sulfate. The solvent was reduced under vacuum and the residue was purified on silica gel to obtain 7 (0.12 g, 96% yield) as a colorless oil. Rf=0.54 (20% ethyl acetate/hexanes. 1H NMR (300 MHz, Chloroform-d) δ 5.74 (dt, J=17.2 Hz, 10.1 Hz, 1H), 5.22-4.93 (m, 2H), 4.29 (d, J=11.9 Hz, 1H), 3.95 (td, J=12.0 Hz, 2.8 Hz, 1H), 3.83-3.73 (m, 2H), 3.35 (s, 3H), 2.26 (td, J=9.9 Hz, 2.2 Hz, 1H), 1.79-1.71 (m, 1H), 1.43 (s, 9H), 1.41 (s, 3H), 1.35 (s, 3H), 1.19-1.07 (m, 1H). 13C NMR (75 MHz, CDCl3) δ 171.3, 132.9, 119.8, 98.2, 81.5, 80.5, 65.9, 60.0, 58.1, 52.3, 29.8, 28.4, 28.1, 19.1.

1. customthen quenched with saturated ammonium chloride (5 mL)
2. extractionThe reaction mixture was extracted with ethyl acetate (3×10 mL)
3. washwashed with brine
4. dry with materialdried over anhydrous sodium sulfate
5. customthe residue was purified on silica gel

ORD record

ord-6fef9167002847d1a29034cec31073c7

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09024038B2