HCID 57124693, compound → HCID 86756674, compound
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[C@H:6]2[CH2:18][C@@H:17]3[O:19][C@:16]3([CH3:20])[C@@H:7]2[C@H:8]([O:11][C:12](=[O:15])[NH:13][CH3:14])[O:9][CH:10]=1)=[O:4]>CO.[OH-].[C+4].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-]>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][O:9][C@@H:8]([O:11][C:12](=[O:15])[NH:13][CH3:14])[C@H:7]2[C@@:16]3([CH3:20])[O:19][C@H:17]3[CH2:18][C@H:6]12)=[O:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
500 mg of (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c] pyrane-4-carboxylic acid methylester descried in Example 3 were dissolved in methanol followed by the suspension of 50 mg of 20 % palladium-carbon hydroxide catalyst and stirring for 12 hours under hydrogen gas atmosphere at 1 atm. After filtering out the insoluble matter, the filtrate was concentrated. The residue was purified by silica gel chromatography to obtain a colorless powder from the hexane-ether eluate in the form of (1S,4R,4aS,6S,7R,7aR)-6,7-epoxy-7-methyl-1-(methylcarbamoyloxy)-1,3,4,4a,5,6,7,7a-octahydrocyclopenta [c] pyrane-4-carboxylic acid methylester (375 mg, yield: 74%), and a colorless powder in the form of (1S,4S,4aS,6S,7R,7aR)-6,7-epoxy-7-methyl-1-(methylcarbamoyloxy)-1,3,4,4a,5,6,7,7a-octahydrocyclopenta [c] pyrane-4-carboxylic acid methylester (68 mg, yield: 14%). The physicochemical properties of the former compound are described in Table 11, Compound No. 55, while those of the latter compound are described in Table 12, Compound No. 56.