Cesium carbonate → HCID 86629211, compound

Participants

Reaction Steps

Suspend 4-bromoguaiacol (1.19 g, 5.72 mmol) and 6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (prepared according to Syn. Comm. V26, Is8, p 1499, 1996) (530 mg, 2.86 mmol) in ethanol (6 mL) and add cesium carbonate (2.33 g, 7.15 mmol) and 18-crown-6 (5 mg). Heat the reaction mixture at reflux temperature for four days. Filter the mixture and evaporate the filtrate. Purify by silica gel chromatography, eluting with 0-65% EtOAc in hexanes to give 760 mg (69%) of the title compound as a yellow solid. 1H NMR (DMSO-d6): δ 7.13 (d, J=2.3 Hz, 1H), 7.04 (dd, J=8.8, 2.3 Hz, 1H), 6.97 (d, J=8.8 Hz, 1H), 5.42 (bs, 1H), 4.54 (m, 1H), 4.10 (m, 1H), 3.74 (s, 3H), 3.54 (td, J=12.6, 4.1, 1H), 3.40 (td, J=12.6, 4.1, 1H), 3.31 (m, 1H), 3.22 (m, 1H), 2.47 (m, 9H).

Provenance & Evidence