Methanol → HCID 22709528, compound

HRID 352878Notes

Reaction equation

HRID 352878 reaction equation
[C:1]([O:5][C:6]([CH:8]1[NH:13][CH2:12][C:11]2[O:14][C:15]([CH:17]=[O:18])=[N:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-]#N.[Na+].[CH3:22][OH:23]>[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6]([CH:8]1[NH:13][CH2:12][C:11]2[O:14][C:15]([C:17]([O:23][CH3:22])=[O:18])=[N:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 8929Sodium CyanideHCID 22709983HCID 22709983, compound

Product 1

HCID 22709528HCID 22709528, compound

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

To a solution of 6-(tert-butoxycarbonyl)-2-formyl-4,5,6,7-tetrahydrooxazol[5,4-c]pyridine (225 mg) in methanol (9.0 ml) were added sodium cyanide (220 mg) and manganese dioxide (780 mg) at room temperature, followed by stirring for 30 minutes. The reaction mixture was subjected to Celite filtration by using ethyl acetate. The filtrate was washed with water (50 ml) and saturated saline (50 ml), dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=3:2→1:1), whereby the title compound (120 mg) was obtained as a colorless transparent glassy substance.

Workup

  1. filtrationThe reaction mixture was subjected to Celite filtration
  2. washThe filtrate was washed with water (50 ml) and saturated saline (50 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=3:2→1:1), whereby the title compound (120 mg)
  7. customwas obtained as a colorless transparent glassy substance

Sources & evidence

ORD record
ord-3b6b53d4ebc849d7933d048da94ad83f
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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