Water → HCID 11230046, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(4-methoxy-benzyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (0.71 mmol) in 2 mL of anhydrous THF is cooled down to −78° C. and freshly prepared LDA (0.85 mmol) is slowly added to the mixture. After the addition, the mixture is allowed to warm up to 0° C., then stirred for 30 minutes and cooled down again to −78° C. Tert-butyl bromoacetate (1.0 mmol) is added. The mixture is stirred at −78° C. for 1 hour and then allowed to warm up to 0° C. To quench the reaction, 1 mL of a mixture of EtOH and water (1:1) is added to the mixture at 0° C. and the mixture is allowed to warm up to room temperature. Water (20 mL) is added followed by extraction (EtOAc, 3×15 mL). The combined organic layers are washed with brine and dried over MgSO4. Solvent is removed under vacuum and the residue is purified by flash column chromatography (silica gel, 0-25% EtOAc/hexane) to provide the desired product [1-(4-methoxy-benzyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl]-acetic acid tert-butyl ester as white solid. Yield: 30%. 1H NMR (400 MHz, CDCl3): δ 7.24 (m, 2H), 7.13 (m, 4H), 6.75 (d, 2H), 5.10 (d, 1H), 4.80 (d, 1H), 2.86(m, 2H), 2.38-2.50(m, 2H), 2.17(q, 1H), 1.80-2.05(m, 2H), 1.40(s, 9H). MS: (ES+): 396 [M+1].

Provenance & Evidence