Potassium Sodium Tartrate → Spiro[cyclobutane-1,3'-indoline]

Participants

Reaction Steps

Add LiAlH4 (266 mg, 7.01 mmol) to a solution of 4-(2-fluoro-phenyl)-tetrahydro-pyran-4-carbonitrile (488 mg, 2.72 mmol) in dimethoxyethane (30 mL). Stir the solution at reflux for 4d, then add aq. Satd Rochelle's salt solution (30 mL) and stir for an additional 1 h at RT. Extract the mixture with Et2O (3×30 mL). Combine the organic extracts and wash with brine (30 mL). Dry, filter and concentrate the organic solution then purify the crude material by flash chromatography, using a linear gradient of 100% hexanes to 30% EtOAc/hexanes, to give the title compound (44 mg, 10%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.31 (m, 1H), 7.03 (dt, 1H, J=1.4, 7.5), 6.79 (dt, 1H, J=0.9, 7.5), 6.64 (d, 1H, J=7.9), 2.36 (m, 2H), 2.21 (m, 2H), 2.02 (m, 2H).

Provenance & Evidence