Sodium Hydroxide → 5-((3aR,6aS)-5-(tert-butoxycarbonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)nicotinic Acid

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Reaction Steps

The product from Example 33A (3.20 g, 8.90 mmol) was dissolved in a solvent mixture of ethanol (40 mL) and water (20 mL). Sodium hydroxide (2.0 M, 13 mL) was added, and the reaction mixture was stirred at ambient temperature for 1 hour. The mixture was then diluted with ethyl acetate (100 mL) and partitioned between ethyl acetate (250 mL) and water (30 mL). The aqueous layer was acidified to pH 4 and repartitioned between dichloromethane (200 mL) and water (250 mL). The organic layer was dried (Na2SO4) and concentrated under vacuum to afford the title compound (3.0 g, 102%). 1H NMR (400 MHz, CD3OD) δ ppm 1.45 (s, 9H), 3.06-3.14 (br s, 2H), 3.27-3.34 (m, 4H), 3.61 (dd, J=10.0, 7.5 Hz, 2H), 3.64-3.71 (m, 2H), 7.57 (dd, J=2.8, 1.8 Hz, 1H), 8.04 (d, J=1.5 Hz, 1H), 8.39 (s, 1H). MS (APCI) m/z 334 (M+H)+.

Provenance & Evidence