HCID 131732503, compound → HCID 123454564, compound

Participants

Reaction Steps

Add 10% palladium on carbon (0.09 g) to a 100 ml Parr bottle. Purge with nitrogen. Add ethanol (5 mL) to wet the catalyst. Add tert-butyl (1S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-[(E)-3-ethoxy-3-oxo-prop-1-enyl]-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylate (330 mg, 0.67 mmol) as a solution in ethanol (15 mL). Seal the bottle and purge with nitrogen. Purge the vessel with hydrogen and pressurize to 414 kPa of hydrogen. Shake at room temperature for 1.5 hours. Vent and open the vessel. Filter the reaction mixture. Concentrate the filtrate under reduced pressure. Purify the residue by silica gel chromatography, eluting with ethyl acetate:hexanes (0-10% gradient) to give the title compound as a clear colorless oil (252 mg, 0.51 mmol). MS (m/z): 392.2 (M-BOC+1).

Provenance & Evidence