Triphenylphosphine → HCID 86627627, compound

Participants

Reaction Conditions

Reaction Steps

Triphenylphosphine (5.16 g) was dissolved in tetrahydrofuran (130 ml) and the solution was cooled to 0° C. under argon. Diisopropylazodicarboxylate (3.82 ml) was added dropwise over 10 min and the resulting mixture was stirred at 0° C. for 20 min (formation of a white precipitate). N-(4-Chloro-2-iodo-phenyl)-2,2,2-trifluoro-acetamide (5.5 g) was added as a solid, followed by 4-hydroxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (J. Org. Chem. 2001, 66, 5545-5551, 3.4 g) dissolved in a minimum volume of tetrahydrofuran. The reaction mixture was allowed to warm to room temperature and stirred for 12 hours. The solution was then concentrated in vacuo and the residue subjected to silica gel chromatography (cyclohexane:ethyl acetate 9:1) to afford 4-{[(4-chloro-2-iodo-phenyl)-(2,2,2-trifluoro-acetyl)-amino]-methyl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (4.7 g). 1H NMR (600 MHz, CDCl3) 1.5 (s, 9H), 2.20 (m, 2H), 3.49 (m, 1H), 3.50 (d, J=17 Hz, 1H), 3.55 (m, 1H), 3.8-3.9 (m, 1H), 5.02 (d, J=17 Hz, 1H), 5.40 (s, 1H), 7.0 (m, 1H), 7.38 (dd, 1H), 7.92 (d, 1H); MS (ES+) 445/447 (M+H+—CO2-isobutene), 486/488 (M+H+-isobutene).

Provenance & Evidence