HCID 13704288, compound → HCID 14511129, compound

HRID 36617Notes

Reaction equation

HRID 36617 reaction equation
[CH3:1][C:2]1([CH3:22])[C@@H:7]([OH:8])[C@H:6]([N:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])[C:5]2[CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=[CH:18][C:4]=2[O:3]1>C(O)C.[Pd]>[NH2:19][C:16]1[CH:17]=[CH:18][C:4]2[O:3][C:2]([CH3:22])([CH3:1])[C@@H:7]([OH:8])[C@H:6]([N:9]3[CH2:13][CH2:12][CH2:11][C:10]3=[O:14])[C:5]=2[CH:15]=1

Participants

4

Reactant 1

HCID 13704288HCID 13704288, compound

Product 1

HCID 14511129HCID 14511129, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 8.0 g (0.025 mol) of trans-3,4-dihydro-2,2-dimethyl-6-nitro-4-(2-oxopyrrolidin-1-yl)-2H-1-benzopyran-3-ol (U.S. Pat. No. 4,647,670) in 800 mL of ethanol is added 2.8 g of 10% Pd/C, and the reaction mixture is stirred under a hydrogen atmosphere for 18 h. The reaction mixture is filtered, evaporated, and the resulting oil subjected to chromatography on silica gel utilizing 4% methanol in dichloromethane as eluent. The eluates are analyzed by thin layer chromatography, and the appropriate fractions are combined and evaporated to afford the title compound.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated
  3. customevaporated

Sources & evidence

ORD record
ord-4e02f4b9987040908d5e8a1e8c051415
Source dataset
uspto-grants-1995_05
Patent number
US05416097

Reaction notes

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