HCID 57124693, compound → HCID 86756674, compound

HRID 1976377Notes

Reaction equation

HRID 1976377 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

HCID 57124693HCID 57124693, compound

Product 1

HCID 86756674HCID 86756674, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 887MethanolSolvent

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.

Workup

  1. filtrationAfter filtering out the insoluble matter
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e2e70ab6e1994fb387ae890088aa863d
Source dataset
uspto-grants-2001_05
Patent number
US06225478B1

Reaction notes

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