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

HRID 602830노트

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HRID 602830 반응식
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

참가 물질

5

반응물 2

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

생성물 1

HCID 53429348Ethyl 1-benzylazetidine-3-carboxylate

시약·촉매·용매 2

HCID 2724098Tetraethylammonium acetate tetrahydrate촉매HCID 962Water용매

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온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-be7c3ba6dee3441884577d6c28b0eb9a
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906549B2

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