Triphenylphosphine → HCID 57310114, compound

Participants

Reaction Conditions

Reaction Steps

N-tert-Butoxycarbonyl-D-homophenylalaninol (1.9 mmol), 2-hydroxyquinoline (2 mmol) and triphenylphosphine (2 mmol) were dissolved in dry THF (20 mL). The solution was cooled to 0° C. and diethyl azodicarboxylate (DEAD) (3.8 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 3 hr, then at room temperature for 16 hr at which time the solvent was evaporated under reduced pressure and the residue purified by chromatography on silica gel (100% CH2Cl2) to give the title compound (240 mg, 33%): 1H NMR (CDCl3) δ 1.46 (9H, s), 1.91-1.99 (2H, m), 2.76-2.81 (2H, m), 4.054.12 (1H, m), 4.51-4.53 (1H, m), 6.91-6.93 (1H, d), 7.19-7.30 (5H, m), 7.37-7.41 (1H, t), 7.61-7.65 (1H, t), 7.72-7.74 (1H, d), 7.82-7.84 (1H, d), 7.99-8.01 (1H, d); MS m/e 393 (100, M+1).

Provenance & Evidence