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

HRID 1644397

Reaction equation

HRID 1644397 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:21]3[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:20]=3[O:19][CH2:18][C:17]2=[O:28])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:31].[Na+]>O.C(OCC)(=O)C.C(OCC)(=O)C.O.[Ru](=O)=O>[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][N:16]2[C:21]3[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:20]=3[O:19][CH2:18][C:17]2=[O:28])[C:12](=[O:31])[CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 56834481tert-Butyl {1-[2-(6-methoxy-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidine-4-yl}carbamate2×

Product 1

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

Reagents, catalysts & solvents 3

HCID 16211523Ruthenium dioxide hydrateCatalystHCID 8857Ethyl AcetateSolventHCID 22728543Water ethylacetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-88411461089d4c5b9e77aa83eb7be2c6
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Linked notes

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