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Alkyne to Alkane

(H2 + Pd/C)







Examples:


Example 1



A solution of the SM (100 mg, 0.385 mmol) in EtOH was degassed by bubbling argon for 2 min. Pd/C (10% wt, 41 mg) was added and the reaction mixture atmosphere was changed to H2 by alternating between vacuum and H2 twice. The reaction was stirred at RT under a H2 filled balloon overnight, after which time the mixture was filtered through celite, concentrated, and purified by flash chromatography (1-10% 7N MeOH/DCM) to provide the product as a colorless oil. [60 mg, 60%] [UK Pat App GB2463151A, page 121]



Example 2



A mixture of the SM (80 mg, 0.23 mmol) and Pd/C (8 mg) in MeOH (5 mL) was stirred under H2 at RT for 16 h. The reaction mixture was filtered, concentrated, and purified by Prep HPLC [5-95% (MeOH)/(H2O with 0.05% TFA)] to provide the product as a yellow solid. [60 mg, 74%]


[Patent Reference: WO2016011390 page 185, (20.2 MB)]



Example 3



The SM (0.27 g, 0.68 mmol) was dissolved in MeOH (10 mL). Pd/C (10%, 0.027 g) was added and the reaction mixture was stirred under H2 at RT for 1 h. The mixture was filtered through a bed of celite, the filter bed was washed with MeOH, and the filtrate was concentrated to provide the product. [0.2 g, 73.5%]


[Patent Reference: WO2015164458, page 107, (6.0 MB)]