Ammonia → HCID 21350205, compound

HRID 1359371Notes

Reaction equation

HRID 1359371 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.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

7

Reactant 4

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

Product 1

HCID 21350205HCID 21350205, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

3.6 g of 2-benzyl-3-methoxymethyloxy-6-iodopyridine (Production Example 12), 1.5 g of (3R,4R)-3,4-dimethylmethylenedioxy-2-pyrrolidinone synthesized by a method known in literature (J. Org. Chem., 1969, 34, 675), 1.1 g of cuprous iodide and 3.3 g of potassium carbonate were suspended in 20 ml of 1-methyl-2-pyrrolidinone, followed by heating stirring at 140° C. for 20 minutes in an oil bath in a nitrogen atmosphere. After cooling as it was, ethyl acetate and aqueous ammonia were added thereto, and the mixture was extracted with ethyl acetate. The organic phase was further washed with brine, dried over anhydrous sodium sulfate anhydride and the solvent was removed. The residue was subjected to silica gel column chromatography using 20-50% ethyl acetate/hexane as an eluent for separation and purification, to give 2 g of the target compound.

Workup

  1. temperatureby heating
  2. temperatureAfter cooling as it
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was further washed with brine
  5. dry with materialdried over anhydrous sodium sulfate anhydride
  6. customthe solvent was removed
  7. customfor separation and purification

Sources & evidence

ORD record
ord-57b576ced1024ed5bcef832d8baf1dec
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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