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Alkene to Alkane

(H2 + HCO2NH4)


Example 1

A 250 mL flask was charged with the SM (3.7 g, 19 mmol), ammonium formate (14 g, 190 mmol), and Pd/C (8.6%, 0.32 g) in MeOH (150 mL). After all the ammonium formate was dissolved, the reaction flask was evacuated and flushed with N2. The reaction mixture was stirred under inert atmosphere (N2) at RT overnight. The mixture was filtered through celite, concentrated in vacuo, diluted with 2M NaOH (ca pH 10), and extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4), and concentrated to provide the crude product which was taken forward without further purification. [3.1 g, 83%, 85:15 α:β]

[Patent Reference: WO2014152144, page 47, (4.6 MB)]

Example 2

A solution of the SM (2.5 g, 7.1 mmol), ammonium formate (2.6 g, 43 mmol), 10% Pd/C (379 mg, 0.3 mmol) in THF (10 mL) and MeOH (30 mL) was refluxed for 90 min. The mixture was filtered through celite and the celite pad was washed with EtOAc. The filtrate was concentrated to provide 3.8 g of material. The material was partitioned between EtOAc/H2O. The org layer was separated, dried (MgSO4), and concentrated to provide the product which was taken to the next step without further purification. [2.2 g, 87%]

[Patent Reference: WO2015144799, page 181, (18.8 MB)]