IL27050A - 3-(tetrahydro-2'-furanyloxy)-steroids of the estrane,androstane and pregnane series,their preparation and use - Google Patents

Description

of and their preparation use PHARMACEUTICAL CORPORATION Of present Invention to tetrahydrofuranyl ethers and the process for their More the present invention relates to ethers of steroids and the process for their The novel compounds of the present invention are represented by one of the following general In the above represents chlorine or represents hydrogen or represents lower or lower aeyloxyi and X represents a carbonyl group or a The compounds of the present invention are prepared by reacting the corresponding compounds in a solvent with at least 1 equivalent of or a ester and a catalytic amount of an After the reaction is the acid is The reaction products may be from ably containing a trace of a suitable material such as When a reaction product of formula I or II contains a this group may be reduced to a hydroxy group by reaction with sodium The compounds of the present invention are effective antilittering agents and are also useful as intermediates in reactions conducted unde conditions since the ether group acts to protest the hydroxy group which it Acid hydrolysis regenerate the hydroxy The following examples illustrate the The ammoniacal water utilized certain of the Examples is a by weight To a 50 flask are added grams of 15 of grams of and about l2 drop of concentrated hydrochloric The flask is loosely stoppered with a polyethylene stopper and is ewirled while being heated to The flask tightly stoppered and permitted to stand for 12 at The solution is alkaline by the addition of of and shaken in a funnel with 15 of methylene chloride and 60 of The organic layer is filtered through anhydrous earhonate and is vacuum to a yellow syrup The crude product is from ing a drop of pyridine to yield grams of in the of faintly white crystals EXAMPLE II Following the procedure of I hut starting with androstenolo e and carrying out the reaction there is obtained upon from et water an yield of in the form of fluffy Following the of Example I hut starting with and allowing the reaction to proceed at room temperature after initial warming there is obtained after recrystallisation from cold hexane followed by a yield of in the form of minute stout The spectrum of this product verified the presence of the Utilising t e procedure I to but starting with the appropriate hydroxyl containing there are IV of 50 of dry grams and drop of concentrated are mixed in a 250 suction flask swirled while being heated to and then stoppered and permitted to stand for 15 hours at To neutralize 8 of is followed by 50 of The mixture is refrigerated for one hour and then the powder with Upon recrystallization from ethanol there is obtained as a in the form of white 1 dram of one by the procedure of Example of sodium borohydride and 20 of absolute ethanol containing a drop of are placed in a The ture is to while being The mixture is then permitted to stand at room temperature 25 of water is added and a rapid solidifying oil is upon r crystallisation from aqueous methanol there is obtained a of as 3 Qraas of by the method of Example II or Example grams of sodium borohydride and 50 of absolute ethanol containing a drop are laced in a 125 flask and heated at for followed precipitation with 120 of There is obtained after froa aqueous methanol grams of in the form of white hairlike fibrous insufficientOCRQuality

Claims (1)

1. CLAIMS Compounds the following is or is hydrogen or is lower alkoxy or and 1 ie a group or a furanylox A method of preparing a compound according to Claim which comprises reacting the corresponding compound in a solvent with at least equivalent of hydrofuran or a ester a catalytic amount of an Processes for compounds according to Claim substantially hereinbefore referenoe to the foregoing use as an agent of a oompound having the formula II er III in Claim insufficientOCRQuality