Sodium triacetoxyborohydride → (3aR,5R,6aR)-Benzyl 5-((3-methoxytetrahydro-2H-pyran-4-yl)amino)-3a-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)hexahydrocyclopenta-[c]pyrrole-2(1H)-carboxylate

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Reaction Steps

A mixture of the product from Step A (difluoroacetate, 97.45 mg, 0.136 mmol), 3-methoxydihydro-2H-pyran-4(3H)-one (35.4 mg, 0.272 mmol), 4 Å molecular sieves (60 mg) and TEA (0.19 mL, 1.36 mmol) in DCM (4 mL) was stirred at rt for 2 h, followed by addition of sodium triacetoxyborohydride (46.12 mg, 0.218 mmol). The resulting mixture was stirred at rt overnight. The reaction was quenched by addition of saturated NaHCO3 aqueous solution, extracted with DCM, dried over Na2SO4. After removal of solvent, the residue was purified by column chromatography (eluent: 5% 7N NH3 in MeOH in DCM) to give the product as a yellow foam. 1H-NMR (400 MHz, CDCl3): δ 1.56-2.12 (m, 7H), 2.31 (br. s., 1H), 2.55-2.67 (m, 1H), 3.06-3.21 (m, 3H), 3.24-4.16 (m, 14H), 4.71 (br. s., 2H), 5.12 (s, 2H), 7.29-7.44 (m, 5H), 7.69 (br. s., 1H), 8.72 (br. s., 1H); LC/MS: C31H37F3N4O5: m/z 603.0 (M+H).

Provenance & Evidence