Sodium Hydroxide → HCID 53911811, compound

HRID 1489168Notes

Reaction equation

HRID 1489168 reaction equation
[CH2:1]([N:8]([CH2:16][C@@:17]1([CH2:27][F:28])[CH2:21][CH2:20][N:19](C(OCC)=O)[CH2:18]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)(C)C>[CH2:1]([N:8]([CH2:16][C@@:17]1([CH2:27][F:28])[CH2:21][CH2:20][NH:19][CH2:18]1)[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54312797HCID 54312797, compound

Product 1

HCID 53911811HCID 53911811, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(S)-3-(N,N-Dibenzylaminomethyl)-1-ethoxycarbonyl-3-fluoromethylpyrrolidine (52 g) was dissolved in isopropyl alcohol (500 ml), and sodium hydroxide (27 g) was added. The mixture was refluxed for 40 hours with stirring. After concentration, water (300 ml) was added to the concentrate and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated to give the object compound as an oil.

Workup

  1. temperatureThe mixture was refluxed for 40 hours
  2. concentrationAfter concentration, water (300 ml)
  3. additionwas added to the
  4. concentrationconcentrate
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-71ecaa261faf45388ac2c5817c626089
Source dataset
uspto-grants-1997_10
Patent number
US05677316

Reaction notes

Loading…