Hydrochloric Acid → HCID 178523816, compound

Temperature

-78 °C

This ketone (2.36 g, 9.55 mmol) in THF (5 mL) was added dropwise to a stirred solution of L-selectride in THF (1M, 19.1 mL, 9.55 mmol) under N2 at -78° C. The reaction mixture was stirred at -78° C. for 3 hours, methanol (0.5 mL) was added, and the reaction mixture was allowed to warm to room temperature. 1N hydrochloric acid (5 mL) was added and the mixture stirred overnight. The reaction mixture was extracted with ethyl acetate (2×20 mL) and the combined organic layers were washed with brine (2×20 mL), dried over anhydrous sodium sulfate, filtered, and the solvent removed in vacuo to yield 2.73 g crude oil. The crude product was purified by MPLC on silica gel (70-230 mesh, 1.5×45 cm column) using a 1:1 hexane/ethyl acetate, 2:1 hexane/ethyl acetate, and ethyl acetate step gradient. Fractions containing pure product were pooled and concentrated in vacuo to give a clear oil (cis-N-Cbz-4-aminocyclohexanol) (1.35 g, 57% yield): 1H NMR (300 MHz) δ 7.35 (m, 5H), 5.10 (s, 2H), 4.74 (br, 1H), 3.91 (br, 1H), 3.62 (br, 1H), 1.18 (m, 8H); MS: (M+H)+ =250, (M+H+NH3)+ =267.

1. temperatureto warm to room temperature
2. stirringthe mixture stirred overnight
3. extractionThe reaction mixture was extracted with ethyl acetate (2×20 mL)
4. washthe combined organic layers were washed with brine (2×20 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. customthe solvent removed in vacuo
8. customto yield 2.73 g crude oil
9. customThe crude product was purified by MPLC on silica gel (70-230 mesh, 1.5×45 cm column)
10. additionFractions containing pure product
11. concentrationconcentrated in vacuo

ORD record

ord-2f5003a4cc6841fabc6bb1e534b91636

Source dataset

uspto-grants-1993_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05190922