Sodium borohydride → HCID 12439096, compound

Participants

Reaction Steps

7-Aza-6-methoxy-1-tetralone is reacted with glyoxylic acid to provide 7-aza-2-carboxy-hydroxymethyl-6-methoxy-1-tetralone and this compound is dehydrated by heating in base to provide 7-aza-2-carboxy-methylidene-6-methoxy-1-tetralone. Saturation of the double bond with zinc in acetic acid followed by acid catalysed esterification with methanol and sulfuric acid provides 7-aza-6-methoxy-2-methoxycarbonylmethyl-1-tetralone. 7-Aza-6-methoxy-2-methoxycarbonylmethyl-1-tetralone to methyl 8-hydroxy-3-methoxy-5,6,7,8-tetrahydro-2-azanaphthalene-7-acetate by reaction with sodium borohydride and reaction of this product with Pd on Carbon/anisole provides methyl-3-methoxy-2-azanaphthalene-7-acetate which is alkylated with methyl iodide and base to provide methyl 3-methoxy-2-azanaphthalene-7-α-methyl-acetate and hydrolysis of this ester provides 3-methoxy-2-azanaphthalene-7-α-methylacetic acid.

Provenance & Evidence