2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → Ethyl 1-benzylazetidine-3-carboxylate

HRID 2035413Notes

Reaction equation

HRID 2035413 reaction equation
CN1CCCN(C)C1=O.[CH2:10]([N:17]1[CH2:20][C:19](C(OCC)=O)([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O.O.O.O.C([O-])(=O)C.C([N+](CC)(CC)CC)C.O>[CH2:10]([N:17]1[CH2:20][CH:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 11483175Diethyl 1-benzylazetidine-3,3-dicarboxylate

Product 1

HCID 53429348Ethyl 1-benzylazetidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 2724098Tetraethylammonium acetate tetrahydrateCatalystHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

Tetraethylammonium acetate tetrahydrate (9.42 g) was added to a 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU, 40 mL) solution of diethyl 1-benzylazetidine-3,3-dicarboxylate (7.00 g, which was prepared according to the method described in Synthetic Communications, volume 33, No. 19, page 3347, 2003), followed by stirring at 130° C. for 12 hours. The reaction solution was added with water, and extracted with an ethyl acetate-hexane (1:1) mixed solvent. The organic layer was washed with water, hexane was added, and extracted with 0.5 mol/L hydrochloric acid. The aqueous layer was washed with tert-butyl methyl ether, and the pH was adjusted to 8 using a 5 mol/L aqueous sodium hydroxide solution, followed by further extraction with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated, to thereby obtain the title compound (3.21 g) having the following physical properties.

Workup

  1. customwas prepared
  2. extractionextracted with an ethyl acetate-hexane (1:1)
  3. additionmixed solvent
  4. washThe organic layer was washed with water, hexane
  5. additionwas added
  6. extractionextracted with 0.5 mol/L hydrochloric acid
  7. washThe aqueous layer was washed with tert-butyl methyl ether
  8. extractionfollowed by further extraction with ethyl acetate
  9. washThe organic layer was washed with brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-0fd94681ff0841beace775b4276afad8
Source dataset
uspto-grants-2013_11
Patent number
US08575134B2

Reaction notes

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