Title:
PREPARATION OF CORTICOID AND PROGESTERONE FROM 17ALPHA-SILYL ETHER OF STEROID
Document Type and Number:
Japanese Patent JP2515967
Kind Code:
B2
Abstract:
PURPOSE: To obtain a new process for the preparation of corticoid and progesterone useful as pharmaceuticals by reacting a specific α-halo silyl ether with a non-nucleophilic base and then, reacting the resulting product with two specific types of reagents.
CONSTITUTION: First, an α-halo silyl ether of formula I [wherein X1 is F, Cl or the like; X2 is Br, CH3 or the like; X3 is H, Cl or the like; X4 is H; X5 is Cl, I or the like; and R16 is =CH2, α-R16-1 (wherein R16-1 is H, F or the like) or the like] [suitably, 17β-cyano-17α-hydroxyandrosta-4,9(11)-dien-3-one.17-(chloro methyl)dimethylsilyl ether or the like] or a 17C epimer thereof is contacted with at least one equivalent non-nucleophilic base which is strong enough to deprotonate the -CX3X4X5 site (preferably, LDA). Then, the reaction mixture is brought into contact with a protiodesilylation agent (e.g. a fluoride ion of BF3 or the like) and a nitrogen to oxygen exchange reagent (suitably, a combination of water and an acid such as HBr) to obtain a desired compound of formula II.
Inventors:
DAGURASU EI RIBINGUSUTON
BURUUSU EI PAARUMAN
SUKOTSUTO DENMAAKU
BURUUSU EI PAARUMAN
SUKOTSUTO DENMAAKU
Application Number:
JP9838495A
Publication Date:
July 10, 1996
Filing Date:
April 24, 1995
Export Citation:
Assignee:
UPJOHN CO
International Classes:
C07F7/18; C07J1/00; C07J75/00; C07J5/00; C07J7/00; C07J41/00; C07J51/00; C07J71/00; (IPC1-7): C07J75/00; C07J7/00
Attorney, Agent or Firm:
Aoyama Ryo (1 person outside)