Methylhydrazine → Tert-butyl 3-(aminooxy)pyrrolidine-1-carboxylate

HRID 1821817노트

반응식

HRID 1821817 반응식
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1.CNN>C(Cl)Cl.CO>[NH2:3][O:12][CH:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1

참가 물질

5

반응물 2

HCID 6061MethylhydrazineHCID 19691445tert-butyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]pyrrolidine-1-carboxylate

생성물 1

HCID 19691331Tert-butyl 3-(aminooxy)pyrrolidine-1-carboxylate수율 77.7%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To an ice-cold solution of tert-butyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]pyrrolidine-1-carboxylate (0.96 g, 2.8 mmol) in CH2Cl2 (16 mL) and MeOH (4 mL) was added methylhydrazine (0.70 mL, 13 mmol) dropwise. The stirred reaction mixture was allowed to slowly warm to ambient temperature. After 2 h, the reaction mixture was concentrated under reduced pressure. To the residue was added CH2Cl2 (20 mL) and with the aid of sonication a solid formed and was collected by vacuum filtration. The filtrate was concentrated and purified by column chromatography (silica gel, 75:25 hexanes/EtOAc to 25:75 hexanes/EtOAc) to afford tert-butyl 3-(aminooxy)pyrrolidine-1-carboxylate (440 mg, 76%): 1H NMR (500 MHz, CDCl3) δ 1.46 (9H, s), 1.82-1.98 (1H, m), 2.04-2.10 (1H, m), 3.31-3.65 (4H, m), 4.24-4.27 (1H, m), 5.37.

후처리

  1. customThe stirred reaction mixture
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue was added CH2Cl2 (20 mL)
  4. customwith the aid of sonication a solid
  5. customformed
  6. filtrationwas collected by vacuum filtration
  7. concentrationThe filtrate was concentrated
  8. custompurified by column chromatography (silica gel, 75:25 hexanes/EtOAc to 25:75 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-9e02d667f66a420995ec24c603a5c40c
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608627B2

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