Hydrochloric Acid → HCID 69294288, compound

HRID 1624361Notes

Reaction equation

HRID 1624361 reaction equation
C(OC([N:6]1[CH2:10][CH2:9][CH:8]([CH2:11][O:12][C:13]([O:15][CH:16]=[CH2:17])=[O:14])[CH2:7]1)=O)=C.[ClH:18]>C(Cl)Cl>[ClH:18].[CH:16]([O:15][C:13](=[O:14])[O:12][CH2:11][CH:8]1[CH2:9][CH2:10][NH:6][CH2:7]1)=[CH2:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59694099HCID 59694099, compound

Product 1

HCID 69294288HCID 69294288, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Vinyloxycarbonyloxymethyl-pyrrolidine-1-carboxylic acid vinyl ester (335 mg, 1.39 mmol) was dissolved in CH2Cl2 (10 mL), and HCl(g) was passed through the solution for 2 minutes then the solution was concentrated in vacuo. The residue was dissolved in MeOH (10 mL) and heated to reflux for 15 minutes then concentrated in vacuo to give a colourless oil (284 mg, 99%). 1H NMR (CD3OD) δ 1.78-1.91 (m, 1H), 2.17-2.28 (m, 1H), 2.79 (m, 1H), 3.09 (dd, 1H, J=12, 7.8 Hz), 3.25-3.51 (m, 3H), 4.19-4.33 (m, 2H), 4.62 (dd, 1H, J=6.2, 2.0 Hz), 4.89 (m, 1H), 7.11 (dd, 1H, J=14, 6.0 Hz).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. dissolutionThe residue was dissolved in MeOH (10 mL)
  3. temperatureheated
  4. temperatureto reflux for 15 minutes
  5. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-671e852fed7d49c990e93ad5b3f27048
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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