Diisopropylethylamine → HCID 59600625, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the triflate (A2) (2.25 g, 5 mmol), methanol (10 ml), N,N-diisopropylethylamine (3 ml), tetrakis(triphenylphosphine)palladium(0) (340 mg), in DMF (20 ml) was degassed and exchanged with carbon monoxide. The mixture was stirred at 50° C. under 1 atmosphere of carbon monoxide for 20 h. After evaporation to remove the excess methanol, the mixture was poured into water, extracted with ether, and purified by flash chromatography to give 1′-tert-butyl 4-methyl 2H-spiro[naphthalene-1,4′-piperidine]-1′,4-dicarboxylate (B1) (1.58 g). LC-MS: m/e=302.0 (M+H—C(CH3)3). Rt=3.82 min. 1H-NMR (500 MHz, DMSO-d6): 7.67 (d, 1H), 7.41 (d, 1H), 7.30 (t, 1H), 7.24 (t, 1 H), 7.00 (t, 1 H), 3.82 (s, H), 3.78 (br. d, 2H), 2.75 (s, 3H), 3.29 (s, 3 H), 3.11 (br. s, 2H), 2.55 (s, 2H), 1.68 (m, 2 H), 1.61 (d, 2H), 1.41 (s, 9H).

Provenance & Evidence