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ChemicalBook CAS DataBase List (3β,20S)-4,4,20-Trimethyl-21-[[tris(isopropyll)silyl]oxy]-pregn-5-en-3-ol 3-Benzoate
552302-70-2

(3β,20S)-4,4,20-Trimethyl-21-[[tris(isopropyll)silyl]oxy]-pregn-5-en-3-ol 3-Benzoate synthesis

5synthesis methods
-

Yield:-

Reaction Conditions:

in pyridine;

Steps:

8.a (20S)-20-[(piperidin-1-yl)methyl]-4,4-dimethyl-5α-pregna-5,7-dien-3β-ol (Compound No. 14)

a) (20S)-4,4 dimethyl-20-[((triisopropylsilyl)oxy)methyl]-prena-5-en-3-ol benzoate 34.4 ml of benzoylchloride were added to a solution of 70 g crude (20S)-4,4-dimethyl-20-[((triisopropylsilyl)oxy)methyl]-pregna-5-en-3β-ol (Example 1c) (not purified by chromatography) in 670 mg pyridine at 0-3° C. The reaction mixture was stirred for 2 h at room temperature and poured into ice-water. The precipitate was filtered off, washed with water and recrystallized from acetone to give 42 g of (20S)-4,4-dimethyl-20-[((triisopropylsilyl)oxy)methyl]-pregna-5-en-3β-ol benzoate. 1H-NMR (CDCl3): δ=8.05 (2H, d); 7.56 (1H, t); 7.45 (2H, t); 5.60 (1H, t); 4.74 (1H, m); 3.68 (1H, dd); 3.36 (1H, m).

References:

US2002/188143,2002,A1