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

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Reaction Steps

A solution of 145 g of [R-(R*,R*)]-alpha-hydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide in 900 mL of 6N HCl was treated with 80 mL of conc. HCl and then was heated at reflux for 2 days. After most of the solvent was removed under reduced pressure, the residue was made decidedly basic with 10N NaOH in an argon atmosphere, and extracted with dichloromethane (1×1.2 L; 2×600 mL). The dried (K2CO3) extracts were evaporated and the crude product was distilled to give 78.5 g of (R)-alpha-methyl-3-pyridinebutanamine, (bp 95° C./0.2 mm).

Provenance & Evidence