Methanol → HCID 86697883, compound

HRID 1529544Notes

Reaction equation

HRID 1529544 reaction equation
I([O-])(=O)(=O)=O.[Na+].[CH2:7]([O:9][C:10]([N:12]1[CH2:17][CH2:16][C:15]2[N:18]=[C:19]([CH:21]([OH:30])C(O)C3C=CC=CC=3)[O:20][C:14]=2[CH2:13]1)=[O:11])[CH3:8].CO>C1COCC1.O>[CH2:7]([O:9][C:10]([N:12]1[CH2:17][CH2:16][C:15]2[N:18]=[C:19]([CH:21]=[O:30])[O:20][C:14]=2[CH2:13]1)=[O:11])[CH3:8]

Participants

6

Reactant 3

HCID 887MethanolHCID 23667635Sodium periodateHCID 66612462HCID 66612462, compound

Product 1

HCID 86697883HCID 86697883, compoundYield 102.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Sodium periodate (1.7 g, 7.8 mmol) was added to a stirred solution of 2-(1,2-dihydroxy-2-phenylethyl)-6,7-dihydro-oxazolo[5,4-c]pyridine-5(4H)-carboxylic acid ethyl ester (1.7 g, 5.2 mmol) in a mixture of THF (34 mL), MeOH (17 mL) and H2O (8.5 mL). The mixture was stirred at room temperature for 2 hours, diluted with H2O and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield 2-formyl-6,7-dihydro-oxazolo[5,4-c]pyridine-5(4H)-carboxylic acid ethyl ester (1.2 g, 99% yield) as a dark oil that was used in the next step without further purification. C10H12N2O4 LCMS: Rt 1.13, m/z 243 [M+H2O+H]+ (using method, LC-MS Method 3).

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-7ca5ddcfb3db4e3bb8828a7eab666314
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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