Ethyl diazoacetate → HCID 59450534, compound

Participants

Reaction Steps

(+)-2,2′-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline (849 mg, 2.542 mmol) was added to a stirring solution of 1H-inden-6-yl benzoate from Step D (30 g, 127.119 mmol) and Cu(I) triflate (657 mg, 1.271 mmol) in dichloromethane (300 mL) at rt under nitrogen. The solution was stirred at rt for 4 h. A solution of ethyl diazoacetate (29 g, 254.237 mmol) in dichloromethane (100 mL) was added at it through a syringe pump over a period of 72 h. Solvent was removed under reduce pressure, and the residue was purified by column chromatography on silica gel (PE) to give the title compound (about 50% enantiomeric excess). 1H-NMR (400 MHz, CDCl3): δ 8.18 (d, J=7.1 Hz, 2H), 7.63 (t, J=7.6 Hz, 1H), 7.51 (t, J=7.1 Hz, 2H), 7.37 (d, J=8.1 Hz, 1H), 6.96-7.02 (m, 2H), 4.16 (q, J=7.1 Hz, 2H), 3.29-3.35 (m, 1H), 2.95-3.10 (m, 2H), 2.46-2.50 (m, 1H), 1.26-1.33 (m, 4H) ppm. MS: m/z 323.2 (M+1)+.

Provenance & Evidence