66876-99-1

Upstream product

• 100-44-7 benzyl chloride 
• 7198-47-2 (4ar,10at)-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazine 
• 53756-97-1 trans-3-(2-hydroxy-ethylamino)-1,2,3,4-tetrahydro-naphthalen-2-ol 
• 66876-97-9 cis-3-[benzyl-(2-hydroxy-ethyl)-amino]-1,2,3,4-tetrahydro-naphthalen-2-ol 

Relevant academic research and scientific papers

Derivatives of the 2-amino-1,2,3,4-tetrahydronaphthalene, IV. Synthesis and configuration of the diastereomeric 2,3,4a,5,10,10a-hexahydro-4H-naphth[2,3-b]-1,4-oxazines ('Naphthalanmorpholines')

The reaction of the trans-hydroxy-amino acid 4 with acetic anhydride in pyridine yielded the trans-azalactone 5, which has been converted into the morpholine derivative trans-3b by LiAlH4 reduction in presence of an excess of borontrifluoride. It has been established in this way that the 'naphthalanmorpholine' (3a) synthesized earlier by L. Knorr on the route 1 → 2a → 3a possesses the trans-configuration. The corresponding cis-isomer of 3a has been obtained by treatment of the aminodiol cis-6c with sulfuric acid and following hydrogenolysis of the N-benzyl group. Therefore, the sulfuric acid dehydration leading to the cyclic ethers 3 occurs stereospecifically.