Azobisisobutyronitrile → tert-butyl ((3aS,5S,6aR)-3a-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)hexahydro-2H-cyclopenta[b]furan-5-yl)carbamate

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Reaction Steps

To a solution of the product of Step E (1.51 g, 2.67 mmol, 1 eq), tris(trimethylsilyl)silane (1.72 mL, 5.34 mmol, 2 eq) and AIBN (438 mg, 2.67 mmol, 1 eq) in benzene (20 mL) was warmed to 80° C. under Ar. After 3 hrs, the solution was concentrated. Purification by chromatography (80 g column) eluting with 50 to 100% EtOAc/heptane afforded the title compound of Step F. 1H NMR (CHLOROFORM-d) δ: 8.72 (br. s., 1H), 7.71 (br. s., 1H), 4.97-5.09 (m, 1H), 4.70-4.91 (m, 2H), 4.56-4.69 (m, 1H), 4.28 (br. s., 1H), 3.80-4.07 (m, 3H), 3.71 (q, J=7.3 Hz, 1H), 3.13 (br. s., 2H), 2.07-2.53 (m, 4H), 1.81 (br. s., 1H), 1.61-1.72 (m, 1H), 1.40 (s, 9H). Calculated for C22H28F3N3O4: 478.2 (M+23). found: 478.2.

Provenance & Evidence