1,4-二溴-2-丁醇 → (4aRS,5SR,8aRS)-1-benzyl-5-(3-hydroxypyrrolidin-1-yl)perhydroquinoxaline-2,3-dione

HRID 1876803

反应方程式

HRID 1876803 反应方程式
[NH2:1][CH:2]1[CH2:11][CH2:10][CH2:9][CH:8]2[CH:3]1[NH:4][C:5](=[O:20])[C:6](=[O:19])[N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+].Br[CH2:27][CH:28]([OH:32])[CH2:29][CH2:30]Br>C(#N)C>[CH2:12]([N:7]1[CH:8]2[CH:3]([CH:2]([N:1]3[CH2:30][CH2:29][CH:28]([OH:32])[CH2:27]3)[CH2:11][CH2:10][CH2:9]2)[NH:4][C:5](=[O:20])[C:6]1=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参与物

5

反应物 3

HCID 295701,4-二溴-2-丁醇HCID 516892碳酸氢钠HCID 68777664(4aRS,5SR,8aRS)-5-amino-1-benzylperhydroquinoxaline-2,3-dione

产物 1

HCID 68778432(4aRS,5SR,8aRS)-1-benzyl-5-(3-hydroxypyrrolidin-1-yl)perhydroquinoxaline-2,3-dione

试剂、催化剂与溶剂 1

HCID 6342乙腈溶剂

实验过程

(4aRS,5SR,8aRS)-5-Amino-1-benzylperhydroquinoxaline-2,3-dione (144 mg, 0.53 mmol) was dissolved in acetonitrile (16 ml), and NaHCO3 (300 mg, 3.57 mmol) and racemic 1,4-dibromobutan-2-ol (purity 85%, 1.15 g, 4.20 mmol, 0.57 ml) were added. After 24 hours, NaHCO3 was separated off and the mixture was evaporated in vacuo. The solid was taken up in CH2Cl2 and the mixture was extracted by shaking three times with HCl (1 N). The aqueous phase was then brought to pH 8 with NaOH (2 N) and extracted by shaking three times with CH2Cl2. The organic phases were dried over Na2SO4 and evaporated in vacuo. The crude product was purified by flash chromatography over silica gel 60 (40-63 μm, (Merck) Ø 2 cm, acetone/MeOH/Et2NH 9.5:0.5:0.1, l=17 cm, V=5 ml). A pale yellow solid was isolated.

后处理

  1. customNaHCO3 was separated off
  2. customthe mixture was evaporated in vacuo
  3. extractionthe mixture was extracted
  4. extractionextracted
  5. stirringby shaking three times with CH2Cl2
  6. dry with materialThe organic phases were dried over Na2SO4
  7. customevaporated in vacuo
  8. customThe crude product was purified by flash chromatography over silica gel 60 (40-63 μm, (Merck) Ø 2 cm, acetone/MeOH/Et2NH 9.5:0.5:0.1, l=17 cm, V=5 ml)
  9. customA pale yellow solid was isolated

来源与证据

ORD记录
ord-7d8d99e8c42741f1b0735069a8d4fb7c
来源数据集
uspto-grants-2012_11
专利号
US08309725B2

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