Sodium Bicarbonate → cis-3-(6-Methoxypyridin-3-yl) 3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

HRID 600720ノート

反応式

HRID 600720 の反応式
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:5]=[N:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=1.[C:13]([N:20]1[CH2:24][CH2:23][CH:22]=[CH:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[C:16]([O:15][C:13]([N:20]1[CH2:24][C@H:23]2[C@H:22]([C:3]([C:4]3[CH:5]=[N:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=3)=[N:2][O:1]2)[CH2:21]1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 10844857tert-Butyl 2,3-dihydro-1H-pyrrole-1-carboxylateHCID 76564447N-Hydroxy-6-methoxy-3-pyridinecarboximidoyl chloride

生成物 1

HCID 68971835cis-3-(6-Methoxypyridin-3-yl) 3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

Chloro oxime 2c (1.12 g; 5.99 mmol), N-Boc-pyrroline (0.5 mL; 2.90 mmol) and sodium bicarbonate (0.61 g) in ethyl acetate (40 mL) were stirred at room temperature for 24 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried (MgSO4), filtered and evaporated to yield crude cycloadduct. 3c was isolated as a white solid after chromatography with 25% ethyl acetate/hexanes.

後処理

  1. washwashed with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto yield crude cycloadduct

出典と根拠

ORDレコード
ord-2f035dffe65f4a80ae0715be7fe1d85d
出典データセット
uspto-grants-2011_03
特許番号
US07902227B2

反応ノート

読み込み中…