Methanol → 5-tert-Butyl 2-methyl 6,7-dihydro[1,3]oxazolo[5,4-c]pyridine-2,5(4H)-dicarboxylate

HRID 459456Notes

Reaction equation

HRID 459456 reaction equation
[C-]#N.[Na+].[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]2[N:17]=[C:18]([CH:20]=[O:21])[O:19][C:13]=2[CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].[CH3:22][OH:23]>[O-2].[O-2].[Mn+4]>[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]2[N:17]=[C:18]([C:20]([O:23][CH3:22])=[O:21])[O:19][C:13]=2[CH2:12]1)=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 8929Sodium CyanideHCID 17842499HCID 17842499, compound

Product 1

HCID 178424645-tert-Butyl 2-methyl 6,7-dihydro[1,3]oxazolo[5,4-c]pyridine-2,5(4H)-dicarboxylate

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

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

Workup

  1. filtrationthe reaction mixture was filtered through Celite with ethyl acetate
  2. washThe filtrate was washed with water (50 ml) and saturated saline (50 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2→1:1)

Sources & evidence

ORD record
ord-a4e928f3468c4c478778ac42a4dcfb93
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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