Acetone → HCID 67264073, compound

Participants

Reaction Steps

Acetone (0.284 mL, 3.86 mmol) was added to a solution of 2-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (0.250 g, 1.29 mmol) in 1,2-Dichloroethane (5 mL), followed by 1.00 M of Titanium tetrachloride in Methylene chloride (1.29 mL). The reaction mixture was stirred for 2 hours. Then, Sodium triacetoxyborohydride (1.36 g, 6.44 mmol) was added and the reaction was stirred overnight. The reaction mixture was diluted with 30 mL DCM, 30 mL saturated sodium bicarbonate and extracted. The organic layer was then concentrated and purified by column chromatography (ISCO 0-60% EtOAc) to give 9-Isopropyl-2-nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene as orange solids (128 mg, 42%). LCMS: 237; 1H-NMR (DMSO): 7.47 (m, 2H), 6.91 (d, 1H, J=8.5 Hz), 4.31 (m, 2H), 3.86 (sept, 1H, J=6.5 Hz), 3.30 (m, 2H), 1.92 (m, 2H), 1.19 (d, 6H, J=6.5 Hz).

Provenance & Evidence