Acetic Acid → 3-Ethylproline hydrochloride

HRID 363212Notes

Reaction equation

HRID 363212 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 (1L), then concentrated in vacuo to give an oil which crystallized upon trituration with ether to give 170 g of the title compound. 1H NMR (D2O) δ4.23 (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 (1L)
  4. concentrationconcentrated in vacuo
  5. customto give an oil which
  6. customcrystallized upon trituration with ether

Sources & evidence

ORD record
ord-4760ef9090db4cbd96102b1bb0e8fab3
Source dataset
uspto-grants-1999_02
Patent number
US05872135

Reaction notes

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