Methanol → HCID 22224442, compound

HRID 638904Notes

Reaction equation

HRID 638904 reaction equation
[N:1]1[N:8]2[C:4]([O:5][C:6]3[CH2:12][O:11][CH2:10][CH2:9][C:7]=32)=[CH:3][C:2]=1[C:13]([O-])=[O:14].[BH4-].[Li+].CO>C1COCC1>[N:1]1[N:8]2[C:4]([O:5][C:6]3[CH2:12][O:11][CH2:10][CH2:9][C:7]=32)=[CH:3][C:2]=1[CH2:13][OH:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 22224494HCID 22224494, compound

Product 1

HCID 22224442HCID 22224442, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the stirred solution of 7,8-dihydro-5H-pyrano[4,3-d]pyrazolo[5,1-b][1,3]oxazole-2-carboxylate (1.5 g, 6.3 mmol) of in 100 ml of THF was added 1.05 g of lithium borohydride and 1.54 g of methanol. The solution was heated at 40 C for 2.5 hour. The reaction was quenched by 1 N HCl, and adjusted to pH 1.3 and stirred at room temperature for 1 hour. The reaction mixture was adjusted pH to 8 with k2CO3. The reaction mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4, and concentrated to an oil and column chromatographed to give 0.74 g of the desired product (60%). (M+H) 196.

Workup

  1. temperatureThe solution was heated at 40 C for 2.5 hour
  2. customThe reaction was quenched by 1 N HCl
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated to an oil and column
  6. customchromatographed

Sources & evidence

ORD record
ord-357337b6bc5345f5b08428fdc83bd47d
Source dataset
uspto-grants-2010_04
Patent number
US07691842B2

Reaction notes

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