Sodium Methoxide → HCID 86622334, compound

Participants

Reaction Steps

Step AC (4): To a solution of (1R,2S)-1-azido-6-methoxy-2,3-dihydro-1H-inden-2-yl 4-nitrobenzoate (248 mg) from Step AC (3) in methanol (2.8 mL) and DCM (2.4 mL) was added sodium methoxide (114 mg), and the reaction mixture was stirred at rt for 30 min. the solvents were removed in vacuo, and water 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-ol compound as a white solid (100 mg). 1H NMR (400 MHz, CDCl3) δ 7.15 (1H, d), 6.91 (1H, d), 6.87 (1H, dd), 4.72 (1H, d), 4.57 (1H, t), 3.80 (3H, s), 3.09 (1H, dd), and 2.84 (1H, dd). The ee of this product was 86% by chiral HPLC (chircel OJ-H column, 4.6×250 mm, 5 μm; mobile phase: 5% ethanol in CO2; flow rate: 2.0 mL/min). Retention time of the title compound: 10.04 min; Retention time of the other enantiomer: 7.38 min.

Provenance & Evidence