Methanol → HCID 21941479, compound

HRID 2216628Notes

Reaction equation

HRID 2216628 reaction equation
[N:1]1[N:9]2[C:4]([O:5][CH2:6][CH2:7][CH2:8]2)=[CH:3][C:2]=1[C:10]([O-])=[O:11].[BH4-].[Li+].CO>C1COCC1>[NH:1]1[N:9]2[CH:4]([O:5][CH2:6][CH:7]=[CH:8]2)[CH2:3][CH:2]1[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 21941385HCID 21941385, compound

Product 1

HCID 21941479HCID 21941479, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the stirred solution of 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate: (4.0 g, 20 mmol) of in 100 ml of THF was added 0.71 g of lithium borohydride and 1.03 g of methanol. The solution was heated at 40 C. for 2.5 hour. The reaction was quenched by 1N 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 chromatographyed to give 2.08 g of the desired product (67%); (M+H) 155.

Workup

  1. temperatureThe solution was heated at 40 C
  2. customThe reaction was quenched by 1N 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

Sources & evidence

ORD record
ord-7456ec4eea5549179c7ad5465221eba7
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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