Hoffmann-La Roche Inc.

Ludwig Labler

Andor Furst

Werner Meier

John William Scott

Paul Buchschacher

The invention is concerned with a process for the preparation of 1 hydrogen or hydroxy cholesterol derivatives and intermediates therefor. The compounds of the present invention are useful as intermediates in the preparation of 24,25-dihydroxy and 1.alpha.,24,25-trihydroxycholecalciferol.

Process for the preparation of cholesterol derivatives and novel

The invention is concerned with a process for the preparation of 1 hydrogen or hydroxy cholesterol derivatives and intermediates therefor. The compounds of the present invention are useful as intermediates in the preparation of 24,25-dihydroxy and 1.alpha., 24,25-trihydroxycholecalciferol.

The present disclosure is directed to a process for the preparation of cholesterol derivatives from corresponding 21-hydroxymethyl steroidal compounds.

Process for the manufacture of cholesterol derivatives

A process for the synthesis of 1.alpha.,3.beta.-dihydroxy-.DELTA..sup.5 -steroids from steroids such as 1.alpha.,2.alpha.-epoxy-cholesta-4,6-dien-3-one, which is reacted with lithium in liquid ammonia in the absence of a proton donator and subsequently reduced by repeated alternative additions of a proton donator, said additions being followed in each case by an equivalent amount of lithium. The final product, a 1.alpha.,3.beta.-dihydorxy-.DELTA..sup.5 -steroid, is useful in the synthesis of derivatives of cholecalciferol.

Process for 1.alpha.,3.beta.-dihydroxy-.DELTA..sup.5 -steroids

The present invention relates to pregnane derivatives of the formula ##STR1## wherein R.sup.1 and R.sup.3 are hydroxyl groups or readily cleavable etherified or esterified hydroxyl groups and R.sup.20 is hydroxymethyl or readily cleavable etherified or esterified hydroxy methyl, formyl, carboxyl or carbalkoxy useful as intermediates for the preparation of 1.alpha.-hydroxycholecalciferols. The present invention also relates to processes for the preparation of the pregnane derivatives and the intermediates thereof.

Pregnane derivatives

Treatment of de-A steroids with a methylation agent at extremely low temperatures, i.e., below -50.degree. C. produces corresponding 10.beta.-methyl-.DELTA..sup.9(11) -deA steroids with a high 10.beta. to 10.alpha. isomer ratio. A number of the product 10.beta.-methyl-.DELTA..sup.9(11) -deA steroids are novel compounds. They are useful as intermediates in the synthesis of known medicinally valuable steroids.

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Allschwil, Switzerland

Ludwig Labler