Dimethylamine → HCID 57210056, compound

HRID 377081Notes

Reaction equation

HRID 377081 reaction equation
[CH3:1][NH:2][CH3:3].ClCCl.[CH3:7][O:8][C:9]([C:11]1[C@H:12]2[CH2:29][C@@H:28]3[O:30][C@:27]3(C)[C@@H:13]2[C@H:14]([O:17][C:18](OC2C=CC=CC=2)=[O:19])[O:15][CH:16]=1)=[O:10]>CCCCCC.C(OCC)(=O)C>[CH3:7][O:8][C:9]([C:11]1[C@H:12]2[CH2:29][C@@H:28]3[O:30][C@@H:27]3[C@@H:13]2[C@H:14]([O:17][C:18](=[O:19])[N:2]([CH3:3])[CH3:1])[O:15][CH:16]=1)=[O:10]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 6344DichloromethaneHCID 57009109HCID 57009109, compound

Product 1

HCID 57210056HCID 57210056, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

5 ml of a 50% aqueous dimethylamine solution were added to a dichloromethane solution containing 198 mg of (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(phenoxycarbonyloxy)cyclopenta[c]pyrane-4-carboxylic acid methylester described in Example 10 followed by stirring for 10 minutes at room temperature. The reaction mixture was then extracted with dichloromethane. After washing the organic phase with brine, it was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a colorless powder from the hexane-ethyl acetate eluate in the form of (1S,4aS,6S,7R,7aR)-1-(dimethylcarbamoyloxy)-6,7-epoxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyrane-4-carboxylic acid methylester (140 mg, yield: 83%). The physicochemical properties of this compound are described in Table 7, Compound No. 31.

Workup

  1. extractionThe reaction mixture was then extracted with dichloromethane
  2. washAfter washing the organic phase with brine, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-64381475e76f4859994da047460f1362
Source dataset
uspto-grants-2000_02
Patent number
US06022888

Reaction notes

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