Ammonium formate → HCID 178501198, compound

Participants

Reaction Steps

A round bottom flask under nitrogen atmosphere was charged with cis-methyl 4-(2-nitro-5-((triisopropylsilyloxy)methyl)phenylamino)cyclohexanecarboxylate (2.77 g, 5.96 mmol) and palladium (10% on carbon) (0.634 g, 0.596 mmol). To this was added EtOH (48.5 mL) followed by ammonium formate (3.76 g, 59.6 mmol). The reaction mixture was stirred at RT for 2 hours and then diluted with EtOH and filtered through Celite® brand filter aid. The filter cake was washed sequentially with DCM (100 mL), EtOH (100 mL), and MeOH (100 mL). The filtrate was concentrated, re-diluted with DCM (100 mL) and washed with brine. The organic layer was collected, dried over sodium sulfate and concentrated to afford cis-methyl 4-(2-amino-5-((triisopropylsilyloxy)methyl)phenylamino)cyclohexanecarboxylate as a brown oil (2.58 g, 100% yield). MS m/z=435.2 [M+H]. Calc'd for C24H42N2O3Si: 434.3.

Provenance & Evidence