Sodium hydride → tert-butyl 4-cyano-3-hydroxy-2,2-dimethyl-2,5-dihydro-1H-pyrrole-1-carboxylate

HRID 1042426노트

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HRID 1042426 반응식
[C:1]([O:5][C:6]([N:8]([CH2:16][CH2:17][C:18]#[N:19])[C:9]([CH3:15])([C:11]([O:13]C)=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].C(Cl)Cl.CCO>O1CCOCC1>[C:18]([C:17]1[CH2:16][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:9]([CH3:10])([CH3:15])[C:11]=1[OH:13])#[N:19]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 21584144Dichloromethane ethanolHCID 57523645methyl N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-2-methylalaninate

생성물 1

HCID 68926013tert-butyl 4-cyano-3-hydroxy-2,2-dimethyl-2,5-dihydro-1H-pyrrole-1-carboxylate수율 85%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

45 g of methyl N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-2-methylalaninate were dissolved in dioxane (240 ml) under nitrogen and 7.9 g of sodium hydride were added. The mixture was refluxed for 6 hours (120° C. internal temperature), and then left to stand overnight at room temperature (TLC: CH2Cl2/EtOH 90/10). The solvent was evaporated, water was added (1000 ml) and the mixture was brought to pH 3-4 with citric acid. The aqueous layer was extracted 4 times with ethyl acetate, the extracts washed with a limited amount of water and evaporated. Then the residue was taken up with hexane, evaporated and crystallized from hexane. 33.1 g of tert-butyl 4-cyano-3-hydroxy-2,2-dimethyl-2,5-dihydro-1H-pyrrole-1-carboxylate were thus obtained (yield: 85%).

후처리

  1. waitleft
  2. customThe solvent was evaporated
  3. additionwater was added (1000 ml)
  4. extractionThe aqueous layer was extracted 4 times with ethyl acetate
  5. washthe extracts washed with a limited amount of water
  6. customevaporated
  7. customevaporated
  8. customcrystallized from hexane

출처 및 근거

ORD 기록
ord-fdb09b030cb843c8aac17f5d7effdcd2
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557857B2

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