Sodium Thiosulfate → tert-butyl ((1S,4S)-4-(2-oxoethyl)-4-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)cyclopent-2-en-1-yl)carbamate

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Reaction Steps

To a solution of the product of Example 1, Step D (417 mg, 0.92 mmol, 1 eq) in DCM (20 mL) at 0° C. was added Dess-Martin periodinane (427 mg, 1.01 mmol, 1.1 eq). After 1 hr, saturated sodium bicarbonate and sodium thiosulfate were added, after 10 minutes, the aqueous was extracted with DCM, the organics combined, dried over MgSO4 and concentrated. Purification by chromatography (12 g column) eluting with 30 to 60% EtOAc/heptane afforded the title compound of Step A. 1H NMR (CHLOROFORM-d) δ: 9.74 (s, 1H), 8.70 (s, 1H), 7.72 (s, 1H), 6.31 (dd, J=5.6, 1.7 Hz, 1H), 5.91 (dd, J=5.6, 1.5 Hz, 1H), 5.01 (d, J=17.1 Hz, 1H), 4.65-4.87 (m, 3H), 4.07-4.21 (m, 1H), 3.79-3.95 (m, 1H), 3.10 (q, J=5.6 Hz, 2H), 3.03 (d, J=16.6 Hz, 1H), 2.63 (dd, J=13.6, 7.2 Hz, 1H), 2.52 (dd, J=16.6, 1.5 Hz, 1H), 2.11 (dd, J=13.1, 7.7 Hz, 1H), 1.44 (s, 9H). Calculated for C22H26F3N3O4: 454.2 (M+1). found: 454.2.

Provenance & Evidence