Acetic Acid → 3-Ethylproline hydrochloride

HRID 2258605Notes

Reaction equation

HRID 2258605 reaction equation
C([N:4]1[CH2:8][CH2:7][CH:6]([CH2:9][CH3:10])[C:5]1(C(OCC)=O)[C:11]([O:13]CC)=[O:12])(=O)C.CC(O)=O.[ClH:25]>>[ClH:25].[CH2:9]([CH:6]1[CH2:7][CH2:8][NH:4][C@@H:5]1[C:11]([OH:13])=[O:12])[CH3:10]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 54461475HCID 54461475, compound

Product 1

HCID 701808173-Ethylproline hydrochloride

Procedure

Diethyl 1-acetyl-3-ethylpyrrolidine-2,2-dicarboxylate (373 g, 0.95 mol) was suspended in 6N HCl (2 L) and HOAc (500 mL) and heated at reflux for 20 h. The reaction mixture was cooled, washed with EtOAc (1 L), then concentrated in vacuo to give an oil which crystallized upon trim ration with ether to give 170 g of the title compound. 1H NMR (D2O) δ 4.23 (d, 1H, J=8 Hz), 3.84 (d, 1H, J=8 Hz), 3.15-3.4 (m, 4H), 2.33-2.44 (m, 1H), 2.19-2.4 (m, 1H), 2.02-2.15 (m, 2H), 1.53-1.72 (m, 3H), 1.23-1.43 (m, 2H), 1.0-1.15 (m, 1H), 0.75-0.83 (m, 6H).

Workup

  1. temperatureat reflux for 20 h
  2. temperatureThe reaction mixture was cooled
  3. washwashed with EtOAc (1 L)
  4. concentrationconcentrated in vacuo
  5. customto give an oil which
  6. customcrystallized upon trim ration with ether

Sources & evidence

ORD record
ord-cefc18f76e9843c591560ac65baefc6a
Source dataset
uspto-grants-1997_08
Patent number
US05661161

Reaction notes

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