HCID 13645761, compound → HCID 13645762, compound

Participants

Reaction Steps

A solution of 3.52 g (10 mmol) of the bromo ester and 1.95 g (30 mmol) NaN3 in 30 ml DMF was stirred overnight at 50°. Upon cooling, the contents were poured into 100 ml H2O and extracted with 2×50 ml Et2O. The organic extracts were washed with brine and dried over MgSO4. Filtration and concentration of the organic material provided 3.09 g crude 1-(3-azidopropyl)-2-phenylcyclohexane carboxylic acid ethyl ester. The crude azide from above (3.09 g) was dissolved in 50 ml EtOH (absolute). Lindlar catalyst (0.5 g) was added and the mixture was subjected to hydrogenation. The solution was filtered through Celite and concentrated in vacuo. The residue was dissolved in Et2O. Dilute hydrochloric acid was added and the organic layer was removed. The aqueous layer was basified and extracted with Et2O (2×50 ml). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to afford 2.43 g crude material. Distillation (140°-143°/0.3 mm) provides 2.40 g (83%) of 1-(3-aminopropyl)-2-phenylcyclohexanecarboxylic acid ethyl ester as a colorless oil.

Provenance & Evidence