2,6-Lutidine → HCID 86675089, compound

HRID 2045794Notes

Reaction equation

HRID 2045794 reaction equation
[CH2:1]([CH:4]1[CH2:13][C:12](=[O:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH:2]=C.I([O-])(=O)(=O)=[O:26].[Na+].N1C(C)=CC=CC=1C>O.O1CCOCC1.[Os](=O)(=O)(=O)=O>[O:14]=[C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[CH:4]([CH2:1][CH:2]=[O:26])[CH2:13]1

Participants

7

Reactant 3

HCID 79372,6-LutidineHCID 21669490HCID 21669490, compoundHCID 23667635Sodium periodate

Product 1

HCID 86675089HCID 86675089, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

Osmium tetroxide (5% in water, 2.0 mL, 0.33 mmol, 0.025 equiv) was added to a biphasic mixture of benzyl 2-allyl-4-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (1A) (4.20 g, 13.1 mmol, 1 equiv), sodium periodate (11.2 g, 52.3 mmol, 4.00 equiv) and 2,6-lutidine (3.04 mL, 26.1 mmol, 2.0 equiv) in water (33 mL) and dioxane (98 mL) at 23° C. The reaction mixture was stirred at 23° C. for 3 h, and then it was partitioned between water and dichloromethane. The aqueous layer was further extracted with dichloromethane (1×), and the combined organic layers were dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash-column chromatography (15% ethyl acetate-hexanes, grading to 70% ethyl acetate-hexanes) to afford 25A. [M+H]+: 324.1

Workup

  1. customit was partitioned between water and dichloromethane
  2. extractionThe aqueous layer was further extracted with dichloromethane (1×)
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationThe dried solution was filtered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash-column chromatography (15% ethyl acetate-hexanes, grading to 70% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-b09d8900733a4c5581260e9db4bb9c35
Source dataset
uspto-grants-2013_11
Patent number
US08592383B2

Reaction notes

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