2,6-Lutidine → HCID 10374484, compound

Participants

Reaction Steps

A mixture of methyl-(S)-(-)-lactate (XXVIII, 2.53 ml) in methylene chloride (130 ml) is cooled to 0°. Triflic anhydride (4.9 ml) is added and the reaction is stirred for 10 minutes at which time 2,6-lutidine (3.55 ml) is added. After an additional ten minutes of stirring at 0°, a mixture of 1-N-(triphenylmethyl)-1,2-diamino-2-methylpropane (XXVII, Step I, 7 g) and triethylamine (4.2 ml) in methylene chloride (50 ml) is added. The reaction is allowed to stir for 1 hr at 0° and 4 hr at 20-25°. After a standard basic workup (methylene chloride, sodium bicarbonate, saline and magnesium sulfate) the residue is chromatographed (silica gel; hexane/ethyl acetate, 4/1), to provide the desired compound, mp 78-80°; IR (mineral oil) 2954, 2924, 2853, 1734, 1457, 1451, 1197 and 709 cm-1 ; NMR (CDCl3) 7.50, 7.24-7.29, 7.17, 3.60, 1.71-2.93, 1.92-2.05, 1.13, 1.08 and, 1.00 δ; MS (m/e) 243, 165, 144 and 84.

Provenance & Evidence