Hydrochloric Acid → HCID 86680030, compound

Participants

Reaction Steps

To a solution of N-(1-benzyl-5-hydroxy-4-methylazepan-4-yl)-2,2,2-trifluoroacetamide (1.7 g, 5.0 mmol) in MeOH (30 mL) was added 1M HCl (1 mL) and palladium hydroxide on carbon (0.25 g). The mixture was shaken under an atmosphere of hydrogen gas (40 psi) for 72 hr. The mixture was filtered through Celite® washing with MeOH (30 mL). The solvent was removed under reduced pressure and the residue passed through an SCX column eluting with (1-10% (7 M NH3 in MeOH)/DCM) to give 2,2,2-trifluoro-N-(5-hydroxy-4-methylazepan-4-yl)acetamide as a yellow gum (0.8 g, 66%). 1H (400 MHz, CDCl3) δ 6.90 (br s, 1H), 4.22-4.16 (m, 1H), 3.70-3.60 (m, 1H), 3.40-3.35 (m, 1H), 3.15-2.99 (m, 1H), 2.90-2.75 (m, 2H), 2.20-2.05 (m, 1H), 1.99-1.75 (m, 4H), 1.53 (s, 3H).

Provenance & Evidence