2,6-Lutidine → HCID 89498402, compound

HRID 1430318Notes

Reaction equation

HRID 1430318 reaction equation
[CH2:1]([O:4][C:5]1([CH2:13][N:14]2[C:18]([CH3:19])=[C:17]([Br:20])[CH:16]=[N:15]2)[CH2:10][CH2:9][CH2:8][C:7]([CH3:12])([CH3:11])[CH2:6]1)[CH:2]=C.CC1C=CC=C(C)N=1.I([O-])(=O)(=O)=[O:30].[Na+]>O1CCOCC1.O.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[Br:20][C:17]1[CH:16]=[N:15][N:14]([CH2:13][C:5]2([O:4][CH2:1][CH2:2][OH:30])[CH2:10][CH2:9][CH2:8][C:7]([CH3:12])([CH3:11])[CH2:6]2)[C:18]=1[CH3:19]

Participants

7

Reactant 3

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 89498376HCID 89498376, compound

Product 1

HCID 89498402HCID 89498402, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of EXAMPLE 180A (2.80 g) in dioxane/water (30 mL/10 mL) was added to 2,6-dimethylpyridine (1.909 mL) and sodium periodate (7.02 g) followed by the addition of osmium tetroxide (2.5% solution, 1.0 mL) and the reaction mixture was stirred for 30 minutes at room temperature. The reaction mixture was diluted with ethyl acetate (50 mL), washed with water (50 mL) and brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. The residue was dissolved in methanol (20 mL) and sodium borohydride (0.16 g) was added. The mixture was stirred at room temperature for 1 hour. An aqueous work up followed by silica gel chromatography using 2-30% ethyl acetate in hexanes provided the title compound.

Workup

  1. washwashed with water (50 mL) and brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in methanol (20 mL)
  6. additionsodium borohydride (0.16 g) was added
  7. stirringThe mixture was stirred at room temperature for 1 hour

Sources & evidence

ORD record
ord-82b7ed272d6a48d99a10d999f4ae112c
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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