Potassium Carbonate → (3aRS, 7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetic acid (5 drops) is added to a solution of 4,4-diphenyl-cyclohex-2-en-1-one (155 g) and N-butoxymethyl-N-trimethylsilylmethyl-benzylamine (202 cc) in dry dichloromethane (1,000 cc) and the reaction mixture is refluxed for 45 minutes. N-Butoxymethyl-N-trimethylsilylmethyl-benzylamine (50 cc) and trifluoroacetic acid (3 drops) are added and the mixture is stirred for a further 45 minutes under reflux before adding further N-butoxymethyl-N-trimethylsilylmethyl-benzylamine (25 cc) and trifluoroacetic acid (3 drops). The reaction mixture is stirred under reflux for 45 minutes and then treated with potassium carbonate (50 g) and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is dissolved in isopropyl ether (200 cc) and the solution is cooled at 0° C. for 1 hour. The crystals are drained, washed with isopropyl ether (2 * 15 cc) and dried to give (3aRS,7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone (193 g) in the form of white crystals melting at 132° C.

Provenance & Evidence