Sodium borohydride → HCID 66609140, compound

HRID 1529545Notes

Reaction equation

HRID 1529545 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]=[C:15]([CH:17]=[O:18])[O:16][C:10]=2[CH2:9]1)=[O:7])[CH3:4]>CO.[Cl-].[Na+].O>[CH2:3]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]=[C:15]([CH2:17][OH:18])[O:16][C:10]=2[CH2:9]1)=[O:7])[CH3:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86697883HCID 86697883, compound

Product 1

HCID 66609140HCID 66609140, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium borohydride (0.71 g, 18.8 mmol) was added to a stirred solution of 2-formyl-6,7-dihydro-oxazolo[5,4-c]pyridine-5(4H)-carboxylic acid ethyl ester (2.82 g, 12.6 mmol) in MeOH (140 mL) at 0° C. The mixture was stirred at room temperature for 20 minutes, diluted with brine and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0 and then MeOH in AcOEt 15/85). The desired fractions were collected and evaporated in vacuo to yield 6,7-dihydro-2-(hydroxymethyl)-oxazolo[5,4-c]pyridine-5(4H)-carboxylic acid ethyl ester (1.8 g, 63% yield) as a colorless oil. C10H14N2O4 LCMS: Rt 0.72, m/z 227 [M+H]+ (using method, LC-MS Method 6).

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica
  7. customThe desired fractions were collected
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-9b234b285e6a4cd9b582379b849de717
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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