Triphenylphosphine → HCID 86755674, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1S,2R,5R,6S)-2-azido-bicyclo [3.1.0]hex-3-ene-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (XXVI) (66 mg, 0.202 mmol) in THF (4.5 mL) and H2O (0.5 mL) was added polymer supported PPh3 (130 mg, 0.404 mmol, 3.1 mmollg) and the mixture was stirred at 60° C. for 19 h. The resin was filtered off and washed with DCM. Removal of the solvent in vacuum left a yellow oil which was purified by silica gel column chromatography with hexane/ethyl acetate 1:3 to give (1S,2R,5R,6S) -2-amino-bicyclo [3.1.0] hex-3-ene-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (XXVII) (19 mg, 31%) as a colorless oil. 1H-NMR (250 MHz, CDCl3) □1.25 (3H, t, J=7.2 Hz), 1.55 (1H, t, J=2.9 Hz), 1.78 (2H, bs), 2.53 (2H, m),4.12 (2H, q,J=7.2 Hz), 5.21 (2H, s), 5.37 (1H, d,J=5.3 Hz), 6.07 (1H, dd,J=5.3, 2 Hz), 7.35 (5H, s); MS[ISP] 302 (M+H+); □D20 -322.98 (c=0.77, CHCl3).

Provenance & Evidence