alphahydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide → (S)-2-Amino-5-(3-pyridyl)pentane

Participants

Reaction Steps

A solution of 160 g of crude [S-(R*,R*)]-alpha-hydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide in 800 mL of 6N HCl was treated with 85 mL conc. HCl and then was heated at reflux overnight as described in Example 16. The crude amine (~85 g), isolated in the normal manner, was distilled to furnish 76.4 g of (S)-alpha-methyl-3-pyridinebutanamine, (60% ee; bp 89°-91°/0.15 mm).

Provenance & Evidence