Ammonium formate → HCID 68325614、化合物

HRID 2403293ノート

反応式

HRID 2403293 の反応式
C1(C(=[N:14][C:15]2[N:20]=[CH:19][C:18]([CH:21]3[O:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]3)=[CH:17][CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])=O.[NH4+]>CO>[NH2:14][C:15]1[N:20]=[CH:19][C:18]([CH:21]2[O:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]2)=[CH:17][CH:16]=1

参加物

4

反応物 2

HCID 2723923Ammonium formateHCID 86671395HCID 86671395、化合物

生成物 1

HCID 68325614HCID 68325614、化合物収率 73.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of tert-butyl (RS)-2-(6-(diphenylmethyleneamino)pyridin-3-yl)morpholine-4-carboxylate (370 mg) in methanol (20 ml) was added ammonium formate (789 mg). The reaction mixture was degassed by bubbling argon into the mixture for several minutes. 10% Palladium on activated charcoal (44 mg) was then added and the reaction mixture was stirred at 60° C. for 1 hour. The reaction mixture was then filtered through celite and the filtrate was concentrated in vacuo. The residue was taken up in EtOAc and the mixture was washed sequentially with water and with saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: heptane/dichloromethane/MeOH) to afford tert-butyl (RS)-2-(6-aminopyridin-3-yl)morpholine-4-carboxylate (171 mg, 73%) as a light yellow oil. MS (ISP): 280.2 ([M+H]+).

後処理

  1. customThe reaction mixture was degassed
  2. customby bubbling argon into the mixture for several minutes
  3. addition10% Palladium on activated charcoal (44 mg) was then added
  4. filtrationThe reaction mixture was then filtered through celite
  5. concentrationthe filtrate was concentrated in vacuo
  6. washthe mixture was washed sequentially with water and with saturated brine
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography (silica gel; gradient: heptane/dichloromethane/MeOH)

出典と根拠

ORDレコード
ord-694f8a67ddcd4c529a1b3c8b0895cfac
出典データセット
uspto-grants-2014_08
特許番号
US08802673B2

反応ノート

読み込み中…