Triphenylphosphine → HCID 18782723, compound

Participants

Reaction Steps

Diethyl azodicaboxylate (3.1 ml, 19.7 mmol) was added dropwise to a solution of 1-benzyl-3-(3-hydroxy-2-tributylstannyl-1-propen-1-yl)piperidin-3-ol (Desc. 2; 8.72 g, 16.26 mmol) and triphenylphosphine (5.12 g, 19.5 mmol) in tetrahydrofuran (100 ml) at -5° C. The cooling bath was removed and the reaction mixture stirred for 45 minutes. The solvent was evaporated, the residue dissolved in acetonitrile (300 ml) and extracted with hexane (3×150 ml). The combined hexane extracts were evaporated and the residue chromatographed on silica, eluting with ethyl acetate/hexane (1:9 then 1:4), to afford the title compound as a colourless oil (5.00 g, 59%); δH (250 MHz, CDCl3) 0.87-0.96 (15 H, m), 1.25-1.35 (6H, m), 1.45-1.60 (11H, m), 1.79 (1H, m), 2.29-2.48 (4H, m), 3.48 (1H, d, J 13.3Hz, NCHZCHBPh), 3.59 (1H, d, J 13.3Hz, NCHACHBPh), 4.67 (2H, m, 2-CH2), 6.03 (1H, br s, 4-CH=), 7.22-7.30 (5H, m ArH).

Provenance & Evidence