Triphenylphosphine → HCID 70145158, compound

Participants

Reaction Steps

A solution of triphenylphosphine (121 g) in THF (1.9 L) was treated with DEAD (80.1 g) over 30 minutes, treated with a solution of Example 3D in DMF (600 mL) at 40° C. by cannula over 90 minutes and a solution of triphenylphosphine (6.2 g) and DEAD (3.8 mL) in THF (20 mL), concentrated, treated with toluene (350 mL), and concentrated. The concentrate was treated with toluene (1.9 L), washed with water, and concentrated to half of its original volume, to provide a solution of (4R)-1-(benzyloxy)-4-((4-bromophenoxy)-methyl)-2-azetidinone. 1H NMR (300 MHz, CDCl3) δ7.4 (m, 7H), 6.70 (m, 2H), 5.00 (d, 1H, J=10), 4.92 (d, 1H, J=12 Hz), 3.86 (m, 1H), 3.82 (dd, 1H, J=1, 4 Hz), 2.81 (dd, 1H, J=6, 15 Hz), 2.66 (dd, 1H, J=2, 15 Hz).

Provenance & Evidence