Acetic Anhydride → HCID 67046148, compound

HRID 132016Notes

Reaction equation

HRID 132016 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].Cl.[CH3:9][N:10]([C@@H:26]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:27][N:28]1CC[C@H:30](O)[CH2:29]1)[C:11](=[O:25])[CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(N(CC)CC)C>[C:5]([O:4][C@H:1]1[CH2:30][CH2:29][N:28]([CH2:27][C@@H:26]([N:10]([CH3:9])[C:11](=[O:25])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:2]1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 9846614Asimadoline hydrochloride

Product 1

HCID 67046148HCID 67046148, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

30 ml of acetic anhydride and 15 ml of triethylamine are added to 5.0 grams (11.0 mmol) of N-methyl-N-[(1S)-1-phenyl-2-((3S)-3-hydroxy-pyrrolidin-1-yl)ethyl]-2,2-diphenylacetamide, hydrochloride, and the mixture is heated for two hours on a steam bath. The reaction mixture is subsequently evaporated to dryness, and the residue is taken up in ether and washed with bicarbonate solution. The organic phase is subsequently dried, and the solvent is distilled off. The resultant residue is purified by column chromatography on silica gel with diethyl ether/methanol (99:1) as eluent. The resultant crude product of N-{2-[(3S)-3-acetoxy-1-pyrrolidinyl]-(1S)-1-phenylethyl}-2,2-diphenyl-N-methylacetamide can be purified further by taking up in diethyl ether, precipitation by addition of ethereal HCl, filtering-off of the resultant crystals under reduced pressure, washing of the crystals with ether and drying in air (Rf=0.6 (TLC on silica gel 6 F254 with dichloromethane/methanol (8:2) as eluent)).

Workup

  1. temperaturethe mixture is heated for two hours on a steam bath
  2. customThe reaction mixture is subsequently evaporated to dryness
  3. washwashed with bicarbonate solution
  4. customThe organic phase is subsequently dried
  5. distillationthe solvent is distilled off
  6. customThe resultant residue is purified by column chromatography on silica gel with diethyl ether/methanol (99:1) as eluent
  7. customThe resultant crude product of N-{2-[(3S)-3-acetoxy-1-pyrrolidinyl]-(1S)-1-phenylethyl}-2,2-diphenyl-N-methylacetamide can be purified further
  8. customprecipitation
  9. additionby addition of ethereal HCl
  10. washfiltering-off of the resultant crystals under reduced pressure, washing of the crystals with ether
  11. dry with materialdrying in air (Rf=0.6 (TLC on silica gel 6 F254 with dichloromethane/methanol (8:2) as eluent))

Sources & evidence

ORD record
ord-4b623baaa60b418d985299f04a3aa531
Source dataset
uspto-grants-2008_06
Patent number
US07385065B2

Reaction notes

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