Water → HCID 68508231, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-fluoro-3-nitro-benzoic acid allyl ester (84.3 g, 0.37 mol, 1.0 equiv) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (75.0 g, 0.37 mol, 1.0 equiv; commercially available) in DMF (500 mL) was added N-ethyldiisopropylamine (111.3 g, 0.86 mol, 2.3 equiv) and the reaction mixture heated at 70° C. for 6 h. The reaction mixture was cooled, poured into water (2 L) and the resulting mixture stirred at rt for 1 h. The precipitate was filtered, washed with water and hexane and finally dried over MgSO4 to obtain 129.1 g (85%) of the title compound. 1H NMR (400 MHz, DMSO): δ 1.46 (s, 9H), 1.46-1.56 (m, 2H), 1.92-1.98 (m, 2H), 2.90-2.98 (m, 2H), 3.88-3.95 (m, 3H), 4.78 (d, J=5.2 Hz, 2H), 5.27 (d, J=10.4 Hz, 1H), 5.38 (d, J=17.3 Hz, 1H), 6.00-6.06 (m, 1H), 7.29 (d, J=9.2 Hz, 1H), 7.99 (dd, J=9.2 Hz, J=1.6 Hz, 1H), 8.24 (d, J=7.8 Hz, 1H), 8.64 (s, 1H).

Provenance & Evidence