Tert-butyl 4-(3,3-dibromoallyl)piperidine-1-carboxylate → Tert-butyl 4-(prop-2-yn-1-yl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 118 mg (0.31 mmol) of 1-(t-butoxycarbonyl)-4-(3,3-dibromoprop-2-enyl)piperidine (from EXAMPLE 74, Step A) in 4 mL of THF at −78° C. was added 0.370 mL (0.92 mmol) of a 2.5 M solution of butyllithium. After stirring at −78° C. for 45 min, the reaction mixture was quenched with 4 mL of sat'd NH4Cl and diluted with 25 mL of ether. After separating the phases, the aqueous layer was extracted with 25 mL of ether. The combined organic phases were washed with 50 mL of sat'd NaCl, dried over MgSO4 and concentrated. The residue was purified by flash chromatography eluting with 4:1 v/v hexanes/ether to give 55 mg (80%) of the title compound: 1H NMR (500 MHz) δ 1.18-1.26 (2H), 1.47 (s, 9H), 1.60-1.67 (m, 11), 1.77 (br d, J=13.2, 2H), 1.99 (t, J=2.6, 11H), 2.16 (dd, J=6.6, 2.5, 2H), 2.68-2.74 (2H), 4.12 (br d, J=13.0,22H).

Provenance & Evidence