The invention relates to monocarbonyl complexes of ruthenium and osmium with bi- and tridentate nitrogen and phosphine ligands. The invention relates to methods for preparing these complexes and the use of these complexes, isolated or prepared in situ, as catalysts for reduction reactions of ketones and aldehydes both via transfer hydrogenation or hydrogenation with hydrogen.

The invention relates to monocarbonyl complexes of ruthenium and osmium with bi- and tridentate nitrogen and phosphine ligands. The invention relates to methods for preparing these complexes and the use of these complexes, isolated or prepared in situ, as catalysts for reduction reactions of ketones and aldehydes both via transfer hydrogenation or hydrogenation with hydrogen.

The invention relates to monocarbonyl complexes of ruthenium and osmium with bi- and tridentate nitrogen and phosphine ligands. The invention relates to methods for preparing these complexes and the use of these complexes, isolated or prepared in situ, as catalysts for reduction reactions of ketones and aldehydes both via transfer hydrogenation or hydrogenation with hydrogen.

Disclosed herein are methods, processes and compositions for preparing a compound of formula 8: (8), and formula 18: (18). The methods and processes comprise performing a first allylic oxidation, a protection reaction, a second allylic oxidation, a reduction reaction, performing an acid-catalyzed coupling reaction, a methylation reaction and a deprotection reaction. Disclosed herein are methods, processes and compositions for enantioselectively preparing compounds of formulae 8 and 18. Also disclosed herein are compositions comprising compounds of formulae 8, 18 and/or intermediates and/or starting material thereof.

##STR00001##

Disclosed herein are methods, processes and compositions for preparing a compound of formula 8: (8), and formula 18: (18). The methods and processes comprise performing a first allylic oxidation, a protection reaction, a second allylic oxidation, a reduction reaction, performing an acid-catalyzed coupling reaction, a methylation reaction and a deprotection reaction. Disclosed herein are methods, processes and compositions for enantioselectively preparing compounds of formulae 8 and 18. Also disclosed herein are compositions comprising compounds of formulae 8, 18 and/or intermediates and/or starting material thereof.

##STR00001##

Disclosed herein are methods, processes and compositions for preparing a compound of formula 8: (8), and formula 18: (18). The methods and processes comprise performing a first allylic oxidation, a protection reaction, a second allylic oxidation, a reduction reaction, performing an acid-catalyzed coupling reaction, a methylation reaction and a deprotection reaction. Disclosed herein are methods, processes and compositions for enantioselectively preparing compounds of formulae 8 and 18. Also disclosed herein are compositions comprising compounds of formulae 8, 18 and/or intermediates and/or starting material thereof.

##STR00001##

Treprostinil is a synthetic prostacyclin derivative with thrombocyte aggregation inhibitory and vasodilatory activity. Treprostinil can be administered in subcutaneous, intravenous, inhalable, or oral forms. Disclosed is a method for the preparation of treprostinil of formula I and its amorphous form, anhydrate form, monohydrate form, and polyhydrate form salts with bases. In the disclosed method, the chiral center in the 3-hydroxyoctyl substituent is formed at the end of the synthesis, so that the method is robust and well scalable. Also disclosed are treprostinil intermediates and the preparation of the intermediates. ##STR00001##

Treprostinil is a synthetic prostacyclin derivative with thrombocyte aggregation inhibitory and vasodilatory activity. Treprostinil can be administered in subcutaneous, intravenous, inhalable, or oral forms. Disclosed is a method for the preparation of treprostinil of formula I and its amorphous form, anhydrate form, monohydrate form, and polyhydrate form salts with bases. In the disclosed method, the chiral center in the 3-hydroxyoctyl substituent is formed at the end of the synthesis, so that the method is robust and well scalable. Also disclosed are treprostinil intermediates and the preparation of the intermediates. ##STR00001##

A method for preparing the borate ester using a lithium compound includes: under the inert gas, stirring and mixing carboxylic acid and borane, and a catalyst lithium compound is added, then the borate ester is obtained with hydroboration; wherein the hydroboration is at room temperature for 10 to 80 min. After the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate esters with different substituents. The lithium compounds are n-butyl lithium, lithium aniline, p-methyl lithium aniline, o-methyl lithium aniline, 2-methoxyaniline lithium, 4-methoxyaniline lithium, 2,6-dimethylaniline lithium, and 2,6-diisopropylaniline lithium. The lithium compounds disclosed in the present invention can catalyze the boron hydrogenation reaction of carboxylic acid and borane with high activity under room temperature conditions; the amount of lithium compound is 0.1-0.9% of the molar amount of carboxylic acid.

A method for preparing the borate ester using a lithium compound includes: under the inert gas, stirring and mixing carboxylic acid and borane, and a catalyst lithium compound is added, then the borate ester is obtained with hydroboration; wherein the hydroboration is at room temperature for 10 to 80 min. After the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate esters with different substituents. The lithium compounds are n-butyl lithium, lithium aniline, p-methyl lithium aniline, o-methyl lithium aniline, 2-methoxyaniline lithium, 4-methoxyaniline lithium, 2,6-dimethylaniline lithium, and 2,6-diisopropylaniline lithium. The lithium compounds disclosed in the present invention can catalyze the boron hydrogenation reaction of carboxylic acid and borane with high activity under room temperature conditions; the amount of lithium compound is 0.1-0.9% of the molar amount of carboxylic acid.