Triphosgene → 3-[(S)-1-(2,5-Dimethyl-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione

Participants

Reaction Steps

The title compound is prepared from 9-{2-[(S)-1-(2,5-dimethyl-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol and triphosgene following a procedure analogous to that described in Step 4 of Intermediate 2; the crude product, a mixture of the title compound and 3-[(S)-1-(2,5-dimethyl-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one, obtained after that is treated as described in Step 10 of Intermediate 2 to convert the intermediate to the title compound, too. Yield: 49% of theory; Mass spectrum (ESI+): m/z=316 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 1.47 (d, J=7.2 Hz, 3H), 1.79-2.00 (m, 5H), 2.05-2.13 (m, 1H), 2.15-2.25 (m, 2H) superimposed by 2.20 (s, 3H) and 2.22 (s, 3H), 2.44-2.55 (m, 2H), 2.70-2.78 (m, 1H), 3.16-3.24 (m, 1H), 5.48 (q, J=7.2 Hz, 1H), 7.02 (dm, J=7.8 Hz, 1H), 7.08 (broad s, 1H), 7.12 (d, J=7.8 Hz, 1H).

Provenance & Evidence