Ammonium Chloride → Cholesta-5,7-diene-1,3-diol

A solution of 51 mg of 20-methyl-1α,3β-bis(methoxycarbonyloxy)-21-p-toluenesulfonyloxypregna-5,7-diene in 1 ml of diethyl ether was added dropwise, at -50° C. to -60° C., to a diethyl ether solution of diisoamylcopper lithium as prepared from 100 mg of cuprous iodide and 0.9 ml of 1.1N diethyl ether solution of isoamyllithium in 2 ml of diethyl ether. reaction mixture was poured into a cold aqueous solution of ammonium chloride and the resulting mixture was extracted with diethyl ether. The extract was washed with 10% aqueous ammonia, water and an aqueous solution of sodium chloride, dried over sodium sulfate and then concentrated. The residue was dissolved in 1 ml of methanol, 10 mg of potassium carbonate was added, and the resulting mixture was stirred at ambient temperature for 12 hours. The reaction mixture was poured into water and extracted with methylene chloride. The extract was washed with an aqueous solution of sodium chloride, dried over sodium sulfate and concentrated. The residue was washed with cold ethyl acetate to give 29 mg of cholesta-5,7-diene-1α,3β-diol.

1. customreaction mixture
2. extractionthe resulting mixture was extracted with diethyl ether
3. washThe extract was washed with 10% aqueous ammonia, water
4. dry with materialan aqueous solution of sodium chloride, dried over sodium sulfate
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in 1 ml of methanol
7. addition10 mg of potassium carbonate was added
8. additionThe reaction mixture was poured into water
9. extractionextracted with methylene chloride
10. washThe extract was washed with an aqueous solution of sodium chloride
11. dry with materialdried over sodium sulfate
12. concentrationconcentrated
13. washThe residue was washed with cold ethyl acetate

ORD-Eintrag

ord-c347a723303646649374acad0c7d4d0e

Quelldatensatz

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05218109