4-Nitrobenzoic Acid → HCID 86622332, compound

Participants

Reaction Steps

Step AC (3): To a solution of (1R,2R)-1-azido-6-methoxy-2,3-dihydro-1H-inden-2-ol (400 mg) from Step AC (2), 4-nitrobenzoic acid (813 mg), triphenyl phosphine (1.28 g) in benzene (10 mL) at rt was added DEAD dropwise (0.77 mL), and the reaction mixture was stirred at rt for 12 h. Saturated sodium bicarbonate was added, the aqueous layer was separated, and the aqueous layer was extracted with EtOAc (×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuo, and the residue was purified by preparative TLC eluting with 30% EtOAc/70% hexanes to give (1R,2S)-1-azido-6-methoxy-2,3-dihydro-1H-inden-2-yl 4-nitrobenzoate compound as a colorless oil (284 mg). NMR (400 MHz, CDCl3) δ 8.28 (2H, dd), 8.22 (2H, dd), 7.20 (1H, d), 6.93 (2H, m), 7.79 (1H, q), 4.94 (1H, d), 3.83 (3H, s), 3.29 (1H, dd), 3.22 (1H, dd).

Provenance & Evidence