Acetic Acid → HCID 54395232, compound

Participants

Reaction Steps

2-Anisaldehyde (0.22 g, 1.60 mmol) was added to a solution of 2-amino-1-benzyltetralin 10 (0.38 g, 1.60 mmol) and acetic acid (0.096 g, 1.60 mmol) in 1,2-dichloroethane (20 mL) and sodium triacetoxyborohydride (0.51 g, 2.40 mmol) under nitrogen. The resulting suspension was stirred for 5 days and then concentrated in vacuo to provide a yellow film. Saturated aqueous potassium carbonate solution (40 mL) and chloroform (40 mL) were added to this material. The layers were separated, and the aqueous layer was extracted with chloroform. The chloroform extracts were combined, dried (Na2SO4), and concentrated to provide 0.51 g of rac-cis-1-(phenylmethyl)-N-(2-methoxyphenylmethyl)-1,2,3,4-tetrahydro-2-naphthalenamine 11 as a brown oil.

Provenance & Evidence