高碘酸钠 → tert-Butyl {1-[2-(6-methoxy-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]-2-oxopiperidin-4-yl}carbamate

HRID 255278

反应方程式

HRID 255278 反应方程式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17][CH2:16]3)[C:7]=2[CH:29]=1.I([O-])(=O)(=O)=[O:31].[Na+]>O.C(OCC)(=O)C.C(OCC)(=O)C.O.[Ru](=O)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][N:15]3[CH2:16][CH2:17][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:19][C:20]3=[O:31])[C:7]=2[CH:29]=1

参与物

6

反应物 2

HCID 23667635高碘酸钠HCID 56834481tert-Butyl {1-[2-(6-methoxy-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidine-4-yl}carbamate2 次

产物 1

HCID 86642633tert-Butyl {1-[2-(6-methoxy-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]-2-oxopiperidin-4-yl}carbamate收率 25%

试剂、催化剂与溶剂 3

HCID 16211523二氧化钌水合物催化剂HCID 8857乙酸乙酯溶剂HCID 22728543Water ethylacetate溶剂

实验过程

A mixture of tert-butyl {1-[2-(6-methoxy-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidin-4-yl}carbamate (Intermediate 47, 1.39 g, 3.4 mmol) in water/ethyl acetate (40 mL, 4:1) was treated with sodium periodate (2.8 g, 21.4 mmol) and ruthenium (IV) oxide hydrate (50 mg, 0.34 mmol) at room temperature. After 53 hours, the reaction was diluted with ethyl acetate, the aqueous phase was extracted with ethyl acetate (6×25 mL), and the combined organic layers were mixed with 2-propanol (20 mL) and stirred for 2 hours at room temperature. The reaction mixture was then filtered through celite, dried over sodium sulfate, and concentrated in vacuo. Chromatography on silica gel with dichloromethane/methanol (95:5) gave 350 mg (25%) of the product as a colorless solid.

后处理

  1. extractionthe aqueous phase was extracted with ethyl acetate (6×25 mL)
  2. additionthe combined organic layers were mixed with 2-propanol (20 mL)
  3. filtrationThe reaction mixture was then filtered through celite
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

来源与证据

ORD记录
ord-bacf811709b04c2b842993bbc11a01b8
来源数据集
uspto-grants-2011_01
专利号
US07875715B2

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