Triphenylphosphine → HCID 10339099, compound

Participants

Reaction Steps

A mixture of Example 1F (28.9 mg, 0.10 mmol), 2-cyclohexen-1-ol (9.8 mg, 0.10 mmol), di-tert-butylazocarboxylate (34.5 mg, 0.15 mmol), triphenylphosphine on polystyrene (3 mmol/g, 50 mg, 0.15 mmol) and THF (2 mL) in a capped 4-mL vial was shaken at room-temperature overnight and filtered. The resin was washed twice with THF (1 mL each) and the combined THF washes were concentrated. The concentrate was purified by preparative HPLC with acetonitrile/water containing 0.1% TFA to provide 4.4 mg (12%) of the desired product. MS (ESI(−)) m/z 368 (M−H)−; 1H NMR (500 MHz, DMSO-d6) δ 10.99 (s, 1H), 10.05 (br s, 1H), 8.92 (s, 1H), 8.73 (s, 1H), 8.27 (d, J=2.5 Hz, 1H), 7.17 (d, J=8.7 Hz, 1H), 7.06 (dd, J=8.9, 2.7 Hz, 1H), 6.01–6.08 (m, 1H), 5.85–5.92 (m, 1H), 4.97–5.04 (m, 1H), 1.89–2.19 (m, 3H), 1.73–1.85 (m, 2H), 1.56–1.68 (m, 1H).

Provenance & Evidence