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

HRID 1821817ノート

反応式

HRID 1821817 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9e02d667f66a420995ec24c603a5c40c
出典データセット
uspto-grants-2009_10
特許番号
US07608627B2

反応ノート

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