Sodium triacetoxyborohydride → HCID 59606201, compound

Participants

Reaction Steps

A mixture of 4-(methylamino)piperidine-1-carboxylic acid tert-butyl ester (200 mg, 0.93 mmol) and oxetan-3-one (56 mg, 0.78 mmol) in DCE (6 mL) was stirred at room temperature for 2 h before the addition of sodium triacetoxyborohydride (264 mg, 1.24 mmol). The resulting mixture was stirred for 16 h, then loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH/DCM and the product eluted with 2M NH3/MeOH. The resulting oil was purified by column chromatography (Si—PCC, MeOH/DCM, 0-20%) affording 4-(Methyl(oxetan-3-yl)amino)piperidine-1-carboxylic acid tert-butyl ester as an oil (40 mg, 16%). 1H NMR (CDCl3, 300 MHz): δ 4.66 (t, J=6.6 Hz, 2H); 4.61 (t, J=6.6 Hz, 2H); 4.16 (s, 2H); 3.95 (p, J=6.6 Hz, 1H); 2.63 (t, J=12.5 Hz, 2H); 2.39 (tt, J=11.7, 3.7 Hz, 1H); 2.20 (s, 3H); 1.60 (d, J=12.5 Hz, 2H); 1.46 (s, 9H); 1.44-1.28 (m, 2H).

Provenance & Evidence