Triphenylphosphine → HCID 86754649, compound

Participants

Reaction Steps

To a stirred solution of N3 -benzoylthymine 20 (1.15 g, 5 mmol) in dry THF (70 ml) under argon was added triphenyl phosphine (2.62 g, 10 mmol) and (2R,4S)-1-(tert-Butyloxycarbonyl)-2-hydroxymethyl-4-phthalimido-pyrrolidine (1.4 g, 4.05 mmol) at room temperature. After 15 min, diethylazodicarboxylate (1.74 g, 10 mmol) was added slowly during 10 min period. The reaction mixture was covered with aluminum foil and allowed to stir at room temperature under argon for 24 h. The solvent was evaporated to dryness and the residue dissolved in EtOAc (150 ml). The organic extract was washed with 5% NaHCO3 solution (100 ml), water (100 ml) and brine (100 ml), and dried over anhydrous Na2SO4. The dried EtOAc extract was evaporated to dryness to give an orange oil. The crude product was purified by flash chromatography over silica gel using hexane→EtOAc as the eluent. The fraction having the required product was pooled and evaporated to give a pale pink oil. Yield: 2.0 g (89%). 1HNMR (CDCl3): 1.41 (s, 9H, Boc), 1.72 (s, 3H, CH3), 1.90 (dd, 1H), 2.34 (m, 1H), 3.40-3.62 (m, 3H), 4.00 (m, 2H), 4.28 (bs, 1H), 4.44 (m, 1H), 7.06 (s, 1H, C6H) and 7.20-7.60 (m, 9H, Ph).

Provenance & Evidence