3-Chloro-2-chloromethyl-1-propene → Benzyl tert-butyl 4-methylidenepyrazolidine-1,2-dicarboxylate

HRID 22666ノート

反応式

HRID 22666 の反応式
[H-].[Na+].[C:3]([NH:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].Cl[CH2:23][C:24]([CH2:26]Cl)=[CH2:25]>CN(C=O)C>[C:18]([O:17][C:15]([N:14]1[CH2:26][C:24](=[CH2:23])[CH2:25][N:13]1[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])=[O:16])([CH3:21])([CH3:20])[CH3:19]

参加物

5

反応物 3

HCID 158593-Chloro-2-chloromethyl-1-propeneHCID 24758Sodium hydrideHCID 11288582Benzyl tert-butyl hydrazine-1,2-dicarboxylate

生成物 1

HCID 12970152Benzyl tert-butyl 4-methylidenepyrazolidine-1,2-dicarboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a suspension of NaH (3.81 g, 95.4 mmol) in DMF (80 mL) is add dropwise a solution of N-Cbz-N′-Boc-hydrazine (12.1 g, 45.4 mmol) in DMF (20 mL). The reaction mixture is stirred about 20 minutes and 3-chloro-2chloromethyl-propene (5.8 mL, 50 mmol) is added dropwise and the reaction is allowed to stir at room temperature until the reaction is complete by TLC, approximately 12 hours. The reaction solution is partitioned between ethyl acetate and water, the water layer being extracted several times more with solvent. The combined organic layers are dried, filtered, and concentrated to afford the desired product as a clear oil which is used without further purification.

後処理

  1. stirringto stir at room temperature until the reaction
  2. customis complete by TLC, approximately 12 hours
  3. customThe reaction solution is partitioned between ethyl acetate and water
  4. extractionthe water layer being extracted several times more with solvent
  5. customThe combined organic layers are dried
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-5ce49e33ff9e4d76b830e4eab483450a
出典データセット
uspto-grants-2005_02
特許番号
US06849627B2

反応ノート

読み込み中…