1-(p-Chlorobenzyl)-alpha,alpha-dimethyl-5-isopropyl-3-cyclopropylmethylthioindole-2-propanoic acid → 1-(p-Chlorobenzyl)-alpha,alpha-dimethyl-5-isopropyl3-cyclopropylmethylthioindole-2-propionamide

Participants

Reaction Steps

To a solution of 110 mg of methyl 1-(p-chlorobenzyl) α,α- dimethyl-5-isopropyl-3-cyclopropylmethylthioindole-2-propanoate (from Example 108) in 1 ml CH2Cl2 was added 1 ml of aminodimethylalane (Me2AlNH2) in hexane/CH2Cl2 (1.0M) and the reaction heated at 65° for 16h. The reaction was quenched with 2N HCl at 0° C., 0.5M NaK tartrate was added and the solution extracted with ether. The product from ether was purified by chromatography on silica gel (Toluene/Acetone/Acetic acid) 85:15:1 to yield the title compound, m.p. 137°-138°.

Provenance & Evidence