Triethylamine → (3R,3aR,6R,6aR)-4-nitrooxy-piperidine-1-carboxylic acid 6-(4-nitro-phenoxycarbonyloxy)-hexahydro-furo[3,2-b]furan-3-yl ester

Participants

Reaction Steps

To a solution of (3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-(nitrooxy)piperidine-1-carboxylate (0.47 g, 1.48 mmol) and Et3N (0.45 g, 4.44 mmol) in THF (25 mL) was added 4-Nitrophenyl chloroformate (0.30 g, 1.48 mmol) as solid. After stirring at rt over night, the mixture was concentrated. The residue was diluted with EtOAc and washed with NaH2PO4 5%. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (Biotage SP1; column SNAP 50; 60% EtOAc in n-hexane), affording the title product as a white solid. 1H-NMR (300 MHz, CDCl3); δ 8.33-8.29 (2H, m), 7.45-7.40 (2H, m), 5.22-5.07 (3H, m), 4.88-4.80 (1H, m), 4.79-4.71 (1H, m), 4.20-3.71 (6H, m), 3.60-3.30 (2H, m), 2.12-1.98 (2H, m), 1.88-1.73 (2H, m).

Provenance & Evidence