Acetyl chloride → 4-Cyclopropyl-1,8-diethyl-2,3,4,9-tetrahydro-1H-carbazole-1-acetic Acid Methyl Ester

Participants

Reaction Conditions

Reaction Steps

The mixture of diastereomeric ketones (40 mmol, 9.52 g) prepared in Step (d) and 2-ethylphenylhydrazine (40 mmol, 5.45 g) were heated at reflux in 172 ml of MeOH for 60 hours, cooled to 0° C. and treated with 80 mmol (6.28 g, 5.7 ml) of AcCl. The reaction was refluxed an additional 45 minutes followed by removal of solvent in vacuo. Flash chromatography afforded 4.58 g (13.5 mmol, 34%) of orange oil containing a mixture of diastereomers.

Provenance & Evidence