Process for the production of (+) biotin

Claim 1

Process for the production of (+) biotin, comprising catalytically hydrogenating a compound of the formula: ##STR23## wherein R 1 is an (R)- or (S)-1-phenylalkyl group, an (R)- or (S)-1-alkoxycarbonyl-1-phenylmethyl group or an (R)- or (S)-1-aryloxycarbonyl-1-phenylmethyl group, and R 2 is hydrogen, a substituted or unsubstituted alkanoyl group, an unsubstituted or a substituted benzoyl group, a substituted or an unsubstituted benzyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an aryloxyalkyl group, an alkoxyalkyl group, a pyranyl group, an unsubstituted or substituted benzenesulfonyl group, an alkylsulfonyl group, a diarylphosphinyl group, a dialkoxyphosphinyl group or a trialkylsilyl group, with hydrogen, separating the desired diastereomer of the formula: ##STR24## if R 2 is H, introducing a protective group by reaction with aliphatic or aromatic acid chlorides, aliphatic or aromatic carboxylic acid anhydrides, haloformic acid alkyl esters, benzyl halides, 1-alkoxyalkyl halides, enol ethers, aromatic or aliphatic sulfonic acid halides, diarylphosphinic acid halides, phosphoric acid dialkyl ester chlorides, trialkylsilyl halides or trialkylsilyl acetamides, converting the diastereomer by a further reaction with a thiocarboxylic acid salt derivative into the corresponding thiolactone, reacting the corresponding thiolactone with a Grignard reagent and subsequently splitting off of water or with a compound of the formula: (C.sub.6 H.sub.5).sub.3 P.sup.⊕ (CH.sub.2).sub.4 COOR.sub.3.X.sup.⊖ III wherein R 3 is H or alkyl with 1 to 4 C atoms and X is a halogen atom, in the presence of a base to a compound of the formula: ##STR25## where R 3 has the above-mentioned meaning, catalytically hydrogenating said compound and then converting said catalytically-hydrogenated compound into (+) biotin by cleavage of the protective groups.