Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → (S)-5-Methoxy-1-methyl-pyrrolidine-2-carboxylic acid phenethyl-amide

HRID 1668421Notes

Reaction equation

HRID 1668421 reaction equation
[CH2:1]([NH:9][C:10]([C@@H:12]1[CH2:16][CH2:15][CH:14]([OH:17])[N:13]1[CH3:18])=[O:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:19]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CO>[CH2:1]([NH:9][C:10]([C@@H:12]1[CH2:16][CH2:15][CH:14]([O:17][CH3:19])[N:13]1[CH3:18])=[O:11])[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 66995346(S)-5-Hydroxy-1-methyl-pyrrolidine-2-carboxylic acid phenethyl-amide

Product 1

HCID 66995375(S)-5-Methoxy-1-methyl-pyrrolidine-2-carboxylic acid phenethyl-amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Product 11B is dissolved hemi-aminal in 10 mL anhydrous methanol and 100 mg 10-camphorsulfonic acid is added. Methanolysis is complete in 1 hour. The resulting material is filtered and concentrated, then reconstituted with ethyl acetate and washed with saturated bicarb followed by drying over anhydrous sodium sulfate, filtered and concentrated. LCMS characterization ES+383.1 (m+1).

Workup

  1. additionis added
  2. filtrationThe resulting material is filtered
  3. concentrationconcentrated
  4. washwashed with saturated bicarb
  5. dry with materialby drying over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ea02397b8c684560b4fb592bcf8002c3
Source dataset
uspto-grants-2011_08
Patent number
US07989441B2

Reaction notes

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