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

HRID 22666노트

반응식

HRID 22666 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5ce49e33ff9e4d76b830e4eab483450a
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849627B2

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