Ammonia → HCID 21350205, compound

HRID 2216352Notes

Reaction equation

HRID 2216352 reaction equation
[CH2:1]([C:8]1[C:13]([O:14][CH2:15][O:16][CH3:17])=[CH:12][CH:11]=[C:10](I)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C@@:20]12[O:28][CH2:27][O:26][N:22]([CH2:23][C@H:24]1[CH3:25])[C:21]2=[O:29].C(=O)([O-])[O-].[K+].[K+].N>CN1CCCC1=O.[Cu](I)I.C(OCC)(=O)C>[CH2:1]([C:8]1[C:13]([O:14][CH2:15][O:16][CH3:17])=[CH:12][CH:11]=[C:10]([N:22]2[CH2:23][C@:24]3([O:26][CH2:27][O:28][C@@:20]3([CH3:19])[C:21]2=[O:29])[CH3:25])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 21350223HCID 21350223, compoundHCID 21942282HCID 21942282, compound

Product 1

HCID 21350205HCID 21350205, compoundYield 54.5%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

3.6 g of 2-benzyl-3-methoxymethyloxy-6-iodopyridine (Production Example 3), 1.5 g of (3R,4R)-3,4-dimethylmethylenedioxy-2-pyrrolidinone synthesized by the known method as described in the literature document (J. Org. Chem., 1969, 34, 675.), 1.1 g of copper iodide (I), and 3.3 g of potassium carbonate were suspended in 20 ml of 1-methyl-2-pyrrolidone, followed by heating under stirring in an oil bath at 140° C. for 20 minutes under nitrogen atmosphere. After standing to cool, ethyl acetate and aqueous ammonia were added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography with 20–50% ethyl acetate/hexane, to give 2 g of the title compound.

Workup

  1. temperatureby heating
  2. temperatureto cool
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed
  7. customthe residue was purified by silica gel column chromatography with 20–50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7f7add79f0044e48b8e24785c9a5b135
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

Loading…