883146-14-3

Upstream product

• 565177-26-6 (1R,5S,6R)-N-(menthol-8-yl)-6-phenyl-3-azabicyclo[3.2.0]heptane 
• 565177-09-5 (2R,2aS,2bS,3aR,5R,7aS,10aR)-2-phenyl-5,8,8-trimethylperhydrocyclobuta[3,4]pyrrolo[2,1-b]-[1,3]benzoxazin-10-one 
• 220985-08-0 N-acryloyl-2α-(2-trans-phenylethenyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 

Downstream Products

• 883146-16-5 1-((1R,5S,6R)-6-phenyl-3-aza-bicyclo[3.2.0]hept-3-yl)-propan-1-one 

Relevant academic research and scientific papers

AZABICYCLOHEPTYL COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE DOPAMINE D3 RECEPTOR

The present invention relates to a compound of the formula (I) wherein R1 is H, C1-C6-alkyl which may be substituted by C3-C6-cycloalkyl, fluorinated C1-C6-alkyl, C3-C6-cycloalkyl, fluorinated C3-C6-cycloalkyl, C3-C6-alkenyl, fluorinated C3-C6-alkenyl, formyl, acetyl or propionyl; A is phenylene, pyridylene, pyrimidylene, pyrazinylene, pyridazinylene or thiophenylene, which can be substituted by one ore more substituents selected from halogen, methyl, methoxy and CF3; E is NR5 or CH2, wherein R5 is H or C1-C3-alkyl; Ar is a cyclic radical selected from the group consisting of phenyl, a 5- or 6-membered heteroaromatic radical comprising as ring members 1, 2 or 3 heteroatoms selected from N, O and S and a phenyl ring fused to a saturated or unsaturated 5- or 6-membered carbocyclic or heterocyclic ring, where the heterocyclic ring comprises as ring members 1, 2 or 3 heteroatoms selected from N, O and S and/or 1, 2 or 3 heteroatom-containing groups each independently selected from NR8, where R8 is H, C1-C4-alkyl, fluorinated C1-C4-alkyl, C1-C4-alkylcarbonyl or fluorinated C1-C4-alkylcarbonyl, and where the cyclic radical Ar may carry 1, 2 or 3 substituents Ra; wherein the variable Ra has the meanings given in the claims and in the description; and physiologically tolerated acid addition salts thereof. The invention also relates to the use of a compound of the formula (I) or a pharmaceutically acceptable salt thereof for preparing a pharmaceutical composition for the treatment of a medical disorder susceptible to treatment with a dopamine D3 receptor ligand.

Synthesis of enantiopure 3-azabicyclo[3.2.0]heptanes by diastereoselective intramolecular [2+2] photocycloaddition reactions on chiral perhydro-1,3-benzoxazines

[2+2] photocycloadditions involving chiral 3-acryloyl-2-vinylperhydro-1,3-benzoxazines derived from (-)-8-aminomenthol are highly diastereoselective reactions. The facial selectivity depends on the type of substitution at the vinyl double bond, and always leads to cis-fused bicyclic derivatives. The de is good for compounds with one substituent at the outer carbon of the double bond at C-2, but only one diastereomer is formed in cyclizations of compounds with two substituents at that position. The elimination of the menthol appendage gives enantiopure 3-azabicyclo[3.2.0]heptanes.