Sodium borohydride → [(1R,2S,4S)-7-oxabicyclo[2.2.1]heptan-2-yl]methanol

温度

0 °C

(1R,2R,4S)-ethyl 7-oxabicyclo[2.2.1]heptane-2-carboxylate (3.63 g, 21.33 mmol) was dissolved in ethanol (107 ml) and cooled to 0° C. Sodium borohydride (4.84 g, 128 mmol) was added portionwise and the reaction was warmed to room temperature and stirred overnight. The reaction was quenched with saturated NH4Cl solution and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 40 g, gradient elution 0-100% EtOAc:Heptane) to afford (1R,2S,4S)-7-oxabicyclo[2.2.1]heptan-2-ylmethanol (0.973 g, 7.59 mmol, 35.6% yield) as a clear colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) δ=4.57 (t, J=5.0 Hz, 1H), 4.49 (d, J=5.1 Hz, 1H), 3.78 (dd, J=6.8, 10.7 Hz, 1H), 3.57 (dd, J=9.3, 10.6 Hz, 1H), 3.51-3.42 (m, 2H), 2.44-2.31 (m, 1H), 2.00-1.92 (m, 1H), 1.85-1.79 (m, 1H), 1.76-1.69 (m, 2H), 1.60 (dd, J=8.6, 12.1 Hz, 1H), 1.49-1.43 (m, 2H), 1.39-1.31 (m, 1H), 1.29-1.24 (m, 1H), 0.94 (dd, J=5.1, 11.9 Hz, 1H)

1. temperaturethe reaction was warmed to room temperature
2. customThe reaction was quenched with saturated NH4Cl solution
3. extractionextracted three times with ethyl acetate
4. washThe combined organic layers were washed with brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe material was purified via column chromatography (RediSep Gold 40 g, gradient elution 0-100% EtOAc:Heptane)

ORDレコード

ord-2e8c0e474cb948c1aa6c9f71af5361ad

出典データセット

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09212182B2