Diisopropylethylamine → HCID 178497349, compound

Participants

Reaction Conditions

Reaction Steps

Pd/C (10 wt. %, 150 mg) was added to a solution of nitro-ester 21a (1.00 g, 3.32 mmol) in DMF (100 mL) and the mixture was hydrogenated at 450 psi for 2 h at ambient temperature. The reaction mixture was filtered through Celite to remove the catalyst and the filtrate was treated immediately with Boc-Py-OBt (27a, 1.42 g, 3.98 mmol) and DIEA (20 mL) and stirred at 60° C. for 18 h. The resulting yellow solution was poured into ice water and extracted with EtOAc. The organic phase was washed with 10% citric acid, brine, and saturated aqueous sodium bicarbonate and dried with MgSO4. Evaporation of the solvent yielded the crude product as a yellow foam which was purified by column chromatography on silica gel (n-hexane/EtOAc 1:2) to give the title compound as a beige solid (409 mg, 25%). 1H NMR (300 MHz, [D6] DMSO): δ=1.45 (s, 9H), 3.82 (s, 3H), 3.87 (s, 3H), 4.16 (s, 3H), 6.88 (s, 1H), 6.99 (s, 1H), 7.60-8.20 (m, 4H), 9.11 (s, 1H), 10.23 (s, 1H), 13.03 (br s, 1H); MS (ESI): m/z: 494 [M+H]+; HR-MS (FAB): calcd for C24H28N7O5: 494.2151; found: 494.2143 [M+H]+.

Provenance & Evidence