Ammonia → 114812-34-9

HRID 1463515Notes

Reaction equation

HRID 1463515 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[C:8]([O:10]CC)=O)[CH3:2].[NH3:13]>CO>[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[C:8]([NH2:13])=[O:10])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10942897Ethyl (S)-(-)-1-Ethyl-2-pyrrolidinecarboxylate

Product 1

HCID 10866443114812-34-9

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl (-)-(S)-1-ethyl-2-pyrrolidinecarboxylate (3.4 g, 0.02 mol) was added to a cooled solution of MeOH (10 ml) and liquid NH3 (10 ml) in a stainless steel reaction bottle containing 3 g of 3 Å molecular sieves. The bottle was heated at 50° C. for 20 h. After cooling the solvent was allowed to evaporate. The product was dissolved in dry MeOH, filtered and the filtrate was evaporated under reduced pressure to give the title compound as white crystals in a quantitative yield (2.8 g). Recrystallization from n-hexane afforded 2.5 g (88%) of the amide, mp 107°-108° C. [α]D25 =-119° (c=0.5 MeOH). The enantiomeric purity was determined to 99.7% S-isomer.

Workup

  1. additioncontaining 3 g of 3 Å molecular sieves
  2. temperatureAfter cooling the solvent
  3. customto evaporate
  4. dissolutionThe product was dissolved in dry MeOH
  5. filtrationfiltered
  6. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7a8b6cc15a5d477fa91e0fe830a34132
Source dataset
uspto-grants-1994_04
Patent number
US05300660

Reaction notes

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