Trifluoroacetic acid → HCID 117772408, compound

Participants

Reaction Steps

To a solution of tert-butyl cis-8-ethoxy-10-(4-fluorophenyl)-11-oxa-3-azaspiro[5.5]undecane-3-carboxylate (510 mg, 1.30 mmol) in CH2Cl2 (1 mL) was added a 1:1 solution of trifluoroacetic acid (1 mL) in CH2Cl2 (1 mL). After 1 hour, the reaction mixture was diluted with aqueous 1 N NaOH (50 mL) and extracted with ethyl acetate (2×50 mL). The organic layers were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide cis-8-ethoxy-10-(4-fluorophenyl)-11-oxa-3-azaspiro[5.5]undecane (520 mg). 1H NMR (400 MHz, CDCl3) δ 7.46-7.31 (m, 2H), 7.10-6.98 (m, 2H), 4.54 (d, J=11.8 Hz, 1H), 3.76 (ddd, J=15.7, 11.3, 4.4 Hz, 1H), 3.66-3.46 (m, 2H), 3.09 (dt, J=13.9, 7.0 Hz, 1H), 2.99-2.76 (m, 3H), 2.69-2.21 (m, 2H), 2.17-2.00 (m, 2H), 1.79-1.64 (m, 1H), 1.64-1.49 (m, 1H), 1.50-1.24 (m, 2H), 1.24-1.12 (m, 3H). ESI-MS m/z calc. 293.18, found 294.5 (M+1)+; Retention time: 0.97 minutes (3 minute run).

Provenance & Evidence