Sodium hydride → Benzyl tert-butyl tetrahydropyridazine-1,2-dicarboxylate

HRID 1108791노트

반응식

HRID 1108791 반응식
[H-].[Na+].[C:3]([NH:10][NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]>CN(C=O)C>[C:3]([N:10]1[CH2:18][CH2:17][CH2:16][CH2:15][N:11]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 11288582Benzyl tert-butyl hydrazine-1,2-dicarboxylate

생성물 1

HCID 21186018Benzyl tert-butyl tetrahydropyridazine-1,2-dicarboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

1.5 g (37.5 mmol) of 60% sodium hydride in oil was suspended in 50 mL of DMF to which was added 5.0 g (18.7 mmol) of 1-Boc-2-Cbz-hydrazine dissolved in 20 mL of dry DMF slowly over 30 minutes. The reaction mixture was stirred for 1 hour until H2 evolution had ceased. To this mixture was added 2.24 mL (18.77 mmol) of 1,4-dibromobutane neat. The reaction mixture was stirred at room temperature over 3 days. The mixture was concentrated in vacuo and the residue was suspended in 150 mL of EtOAc. The mixture was washed with water twice, 5% citric acid twice, saturated aqueous NaHCO3 solution , water and brine. The solution was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography over silica gel eluting with 30% EtOAc/hexanes to give the desired product as a white solid. 1H-NMR (CDCl3, 400 MHz):1.45 (bs, 9H); 1.62 (bm, 4H); 2.90 (bs, 2H); 4.15 (bm, 2H); 5.00-5.30 (m, 2H); 7.20-7.40 (bm, 5H).

후처리

  1. stirringThe reaction mixture was stirred at room temperature over 3 days
  2. concentrationThe mixture was concentrated in vacuo
  3. washThe mixture was washed with water twice
  4. dry with materialThe solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography over silica gel eluting with 30% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-286610baa8e7499da66654a1fb83ab1b
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06069163

반응 노트

불러오는 중…