Tert-butyl 4-cyano-4-(cyclopropylmethyl)piperidine-1-carboxylate → 4-(Cyclopropylmethyl)piperidine-4-carbonitrile

Participants

Reaction Steps

A solution of tert-butyl 4-cyano-4-cyclopropylmethylpiperidine-1-carboxylate (I-2) (1.00 g, 3.78 mmol) in TFA (50 mL) and DCM (75 mL) was stirred at room temperature for 0.5 h then the volatile components removed in vacuo. The residue was partitioned between saturated sodium bicarbonate solution and DCM. The organic phase was separated and the aqueous phase re-extracted with DCM twice. The combined organic phase was washed with brine, dried (MgSO4) and the solvent removed in vacuo to leave 4-cyano-4-cyclopropylmethylpiperidine (I-8) as a glass. 1H NMR (500 MHz, CD3OD): δ 3.03 (d, J=13.1 Hz, 2 H), 2.88-2.82 (m, 2 H), 2.00 (d, J=11.7 Hz, 2 H), 1.55-1.49 (m, 4 H), 0.92-0.84 (m, 1 H), 0.57-0.55 (m, 2 H), 0.20 (q, J=5.0 Hz, 2 H).

Provenance & Evidence