Reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[C:3](=[O:8])[NH:2]2.Cl.N[C@@H]1C[C@H:14]([C:16]([OH:18])=O)C=C1.[CH3:19][OH:20]>C(OC(=O)C)(=O)C.N1C=CC=CC=1>[CH3:19][O:20][C:3]([C@H:4]1[CH2:7][C@@H:1]([NH:2][C:16](=[O:18])[CH3:14])[CH:6]=[CH:5]1)=[O:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Acidic hydrolysis of 2-azabicyclo[2.2.1]hept-5-en-3-one (1, referring to the corresponding number on the flow sheet) to cis-4-aminocyclopent-2-ene carboxylic acid hydrochloride, followed by esterification of the carboxyl function in refluxing methanol and subsequent acetylation of the amino group in acetic anhydride-pyridine, gives methyl-cis-4-acetamidocyclopent-2-ene carboxylate (2). Reduction of the methyl ester of 2 gives, after acetylation, acetate 3. Epoxidation of acetate 3 is stereoselective due to the syn-directing allylic amide group, giving only the cis-epoxide 4. Hydrolysis of the epoxide 4 and subsequent acetylation gives a mixture of 5, 6 and 6a.
Sources & evidence
- ORD record
- ord-841c6861a0c148949ec2508d2f25a3b3
- Source dataset
- uspto-grants-1983_05
- Patent number
- US04383114
Linked notes
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