tert-Butanol → HCID 18926568, compound

Participants

Reaction Conditions

Reaction Steps

Diphenylphosphoryl azide (3.99 g) was added to a stirred mixture of methyl 5-(2-carboxyethyl)-2-methyl-3-(3-pyridylmethyl)-1H-indole-1-propanoate (5.00 g) and triethylamine (1.46 g) in dry t-butanol (30 ml) and the mixture was heated at 100° C. for 18 hours and then evaporated. Theresidue was dissolved in dichloromethane, and the solution was washed twicewith water and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel. Elution with dichloromethane and evaporation of the product fractions gave the title compound as a gum (4.51 g), Rf. 0.35(SS4). δ(CDCl3): 1.42(9H,s), 2.37(3H,s), 2.73(2H,t), 2.82(2H,t), 3.36(2H,m), 3.68(3H,s), 4.05(2H,s), 4.39(2H,t), 4.50(1H,br), 7.00(1H,d), 7.10-7.25(3H,m) 7.41 (1H,d), 8.39(1H,d), 8.50(1H,s).

Provenance & Evidence