GB813845A - Improvements in cyclopentanophenanthrene compounds - Google Patents
Improvements in cyclopentanophenanthrene compoundsInfo
- Publication number
- GB813845A GB813845A GB9567/56A GB956756A GB813845A GB 813845 A GB813845 A GB 813845A GB 9567/56 A GB9567/56 A GB 9567/56A GB 956756 A GB956756 A GB 956756A GB 813845 A GB813845 A GB 813845A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diol
- androstene
- androsten
- acetic acid
- acetate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises cyclopentanophenanthrene compounds of the general formula <FORM:0813845/IV (b)/1> wherein X represents hydrogen or a methyl, ethyl, propyl, butyl, amyl, isoamyl, vinyl, cyclopentylpropionyl, palmitoyl, benzyl, tolyl or naphthyl radical, and the preparation thereof by reducing D 5-androsten-3b -ol-16-one or the required 3-carboxylic ester or ether thereof with an alkali metal borohydride or an alkali metal aluminium hydride. The above process may be modified in that the D 5-androsten-3b ,16b -diol is subsequently acylated or etherified in the 3- and 16-positions or a 3-carboxylic ester or ether of D 5-androstene-3b ,16b -diol may be acylated or etherified in the 16-position. The above process may also be modified in that the D 5-androstene-3b ,16b -diol is reacted with an aryl sulphonyl halide to form D 5-androstene-3b ,16b - diol - di - arylsulphonate, the di-arylsulphonate is selectively hydrolysed with dilute sulphuric acid to form D 5-androstene-3b ,16b -diol-16-arylsulphonate, the 16-arylsulphonate is reacted with an alkali metal acetate in acetic acid to form the 16-acetic acid ester of D 5-androstene-3b ,16a -diol which is then hydrolysed to form D 5-androstene-3b ,16a -diol, or the 3-carboxylic ester or ether of D 5-androstene-3b ,16b -diol is reacted with an aryl sulphonyl halide to form the corresponding 16-arylsulphonic acid ester, this ester is reacted with an alkali metal acetate in acetic acid to form the corresponding 16-acetic acid ester of the 3-carboxylic ester or ether of D 5-androstene-3b ,16a -diol which is then hydrolysed to form D 5-androstene-3b ,16a -diol or to the 3-ether thereof. The additional modified processes referred to above may be extended by acylating or etherifying D 5 - androstene - 3b ,16a - diol in the 3-and 16-positions, or by acylating or etherifying a 3-ether of D 5-androstene-3b ,16a -diol in the 16-position. In the examples: (1) D 5-androstene-3b ,16b -diol is prepared by reducing D 5-androsten - 3b - ol - 16 - one with sodium borohydride and is converted into the corresponding diacetate and dibenzoate; (2) D 5-androstene - 3b ,16a - diol is prepared by reacting D 5 - androstene - 3b ,16b - diol with p-toluene sulphonyl chloride to form D 5-androstene - 3b ,16b - diol - di - p - toluene sulphonate, partially hydrolysing the di-sulphonate to form D 5-androstene-3b ,16b -diol-16-p-toluene sulphonate, epimerizing the monosulphonate by heating with acetic acid and sodium acetate to form D 5 - androstene - 3b ,16a - diol - 16 - acetate and hydrolysing the 16-acetate; (3) D 5 - androstene - 3b ,16a - diol is prepared by acetylating D 5-androsten-b -ol-16-one to form 3b -acetoxy- D 5-androsten-16b -ol, treating this compound with p-toluenesulphonyl chloride to form D 5 - androstene - 3b ,16b - diol - 3 - acetate-16 - p - toluenesulphonate, heating this compound with sodium acetate and acetic acid to form D 5 - androstene - 3b ,16a - diol - diacetate and acetic acid to form D 5-androstene-3b ,16a -diol-diacetate and then hydrolysing this product to form the required diol, and, if necessary, esterifying the diol to form the diacetate or dibenzoate thereof; (4) 3b -methoxy- D 5-androsten-16b -ol is prepared by reducing 3-methoxy-D 5-androsten-16-one with sodium borohydride; (3) 3b - methoxy - D 5 - androsten - 16a - ol is prepared by treating 3b -methoxy- D 5-androsten-16b -ol with p-toluenesulphonyl chloride to form the corresponding 16-p-toluenesulphonate, fusing the sulphonate with sodium acetate in acetic acid to form 3b -methoxy-16a -acetoxy-D 5-androstene, and hydrolysing this compound to form the desired 16a -ol. Specification 813,333 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US813845XA | 1955-08-01 | 1955-08-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB813845A true GB813845A (en) | 1959-05-27 |
Family
ID=22163804
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB9567/56A Expired GB813845A (en) | 1955-08-01 | 1956-03-27 | Improvements in cyclopentanophenanthrene compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB813845A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3939186A (en) * | 1973-12-29 | 1976-02-17 | Mitsubishi Chemical Industries Limited | Process for producing ethers of steroids |
US6187925B1 (en) | 1997-12-23 | 2001-02-13 | Merck & Co., Inc. | Intermediates and process for the synthesis of azasteroids |
-
1956
- 1956-03-27 GB GB9567/56A patent/GB813845A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3939186A (en) * | 1973-12-29 | 1976-02-17 | Mitsubishi Chemical Industries Limited | Process for producing ethers of steroids |
US6187925B1 (en) | 1997-12-23 | 2001-02-13 | Merck & Co., Inc. | Intermediates and process for the synthesis of azasteroids |
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