Diiodomethane → HCID 67251932、化合物

温度

0 °C

To a −20° C. solution of intermediate diisopropyl (4S,5S)-2-[(1E)-prop-1-enyl]-1,3-dioxolane-4,5-dicarboxylate (4.10 g, 14.32 mmol) in 60 mL hexanes was added 1M diethylzinc in hexanes (42.96 mL, 42.96 mmol). Diiodomethane (6.92 mL, 85.92 mmol) was added dropwise with vigorous stirring. After 1 h at −20° C., the reaction was refrigerated at −5° C. After 17 h at −5° C., the reaction was stirred at 0° C. for an additional 5 h and then quenched with cold saturated ammonium chloride solution (100 mL) and extracted with Et2O (100 mL×3). The combined organics were washed w/aqueous sodium thiosulfate (100 mL) and brine (100 mL), filtered, dried over Na2SO4, filtered again and concentrated in vacuo. Purification by normal phase chromatography (10->30% EtOAc/hexanes) yielded 3.85 g (89%) of diisopropyl (4S,5S)-2-[(1S,2S)-2-methylcyclopropyl]-1,3-dioxolane-4,5-dicarboxylate as a yellow oil. 1H NMR (CDCl3, 400 MHz) 5.12 (m, 2H); 4.78 (d, J=6.41 Hz, 1H); 4.66 (d, J=4.21 Hz, 1H); 4.57 (d, J=4.22 Hz, 1H); 1.30 (m, 12H); 1.09 (d, J=5.68 Hz, 3H); 0.94 (m, 2H); 0.67 (m, 1H); 0.39 (m, 1H); LC/MS [M+H]+=301.

1. customwas refrigerated at −5° C
2. waitAfter 17 h at −5° C.
3. customquenched with cold saturated ammonium chloride solution (100 mL)
4. extractionextracted with Et2O (100 mL×3)
5. washThe combined organics were washed w/aqueous sodium thiosulfate (100 mL) and brine (100 mL)
6. filtrationfiltered
7. dry with materialdried over Na2SO4
8. filtrationfiltered again
9. concentrationconcentrated in vacuo
10. customPurification by normal phase chromatography (10->30% EtOAc/hexanes)

ORDレコード

ord-a3dc17cecd58469f8a2bfa56acfbf188

出典データセット

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07968571B2