Ammonium formate → HCID 86749589, compound

Participants

Reaction Steps

Part A: Nitrogen gas was bubbled through methanol (25 mL). The following reagents were added in order: 10% palladium on carbon (0.5 g), the product of Example 8 (0.5 g, 1.5 mmol) and ammonium formate (1.0 g). The reaction mixture was heated to reflux temperature and stirred for 30 min. The reaction mixture was cooled to ambient temperature and filtered through Celite. The filter pad was washed with methanol and chloroform. The combined filtrates were concentrated in vacuo. The residue was treated with a 1N NaOH solution and extracted three times with ethylacetate. The combined organic layers were dried over magnesium sulfate and filtered. Solvent was removed in vacuo to give cis-6-(4'-fluorophenyl)-6-hydroxydecahydroisoquinoline: NMR (CDCl3, 300 MHz): 7.45 (dd, 2H, J=8, 6), 7.0 (t, 2H, J=8), 3.15-1.4 (m, 16H); HRMS: Calcd: 249. 1529 Found: 249.1531.

Provenance & Evidence