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

HRID 2035413ノート

反応式

HRID 2035413 の反応式
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

参加物

5

反応物 2

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

生成物 1

HCID 53429348Ethyl 1-benzylazetidine-3-carboxylate

試薬・触媒・溶媒 2

HCID 2724098Tetraethylammonium acetate tetrahydrate触媒HCID 962Water溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0fd94681ff0841beace775b4276afad8
出典データセット
uspto-grants-2013_11
特許番号
US08575134B2

反応ノート

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