Isoamyl Nitrite → 3-Amino-2-hydroxybornane

Participants

Reaction Steps

These compounds can be synthesized as follows. D-camphor or L-camphor is reacted with isoamyl nitrite in the presence of metallic sodium, and the product is reduced with lithium aluminum hydride to obtain 3-amino-2-hydroxybornane. The resulting 3-amino-2-hydroxybornane is reacted with furoyl chloride, 2-thiophenecarbonyl chloride-, or benzoyl chloride in the presence of pyridine or 4-dimethylaminopyridine, or it is subjected to a dehydrating reaction with furfural, 1-methyl-2-pyrrolecarbaldehyde, 1-benzyloxycarbonyl-L-proline, or benzaldehyde in the presence of a dehydrating agent. The resulting product is then reduced with lithium aluminum hydride to obtain a 3-amino-2-hydroxybornane derivative of exo or endo form.

Provenance & Evidence