Methanol → {4H,5H,6H-pyrrolo[1,2-b]pyrazol-2-yl}methanol

HRID 2216562Notes

Reaction equation

HRID 2216562 reaction equation
CO.[Li+].[BH4-].C([O:7][C:8]([C:10]1[CH:11]=[C:12]2[CH2:17][CH2:16][CH2:15][N:13]2[N:14]=1)=O)C>C1COCC1>[N:14]1[N:13]2[CH2:15][CH2:16][CH2:17][C:12]2=[CH:11][C:10]=1[CH2:8][OH:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 12841166ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate

Product 1

HCID 21941359{4H,5H,6H-pyrrolo[1,2-b]pyrazol-2-yl}methanolYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

MeOH (2.73 mL) was added to the THF (180 mL) solution of LiBH4 (1.63 g) under a nitrogen atmosphere at room temperature, and then 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylic acid ethyl ester (8.11 g) was added to the suspension and stirred for 2 h at 40° C. The mixture was quenched with 1 mol/L HCl at pH 1 and stirred for 1 h at room temperature. Solid K2CO3 was added to the solution to adjust pH to 8 and the mixture was extracted with AcOEt. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to afford the title compound as brown crystals (4.87 g, 78%).

Workup

  1. customThe mixture was quenched with 1 mol/L HCl at pH 1
  2. stirringstirred for 1 h at room temperature
  3. additionSolid K2CO3 was added to the solution
  4. extractionthe mixture was extracted with AcOEt
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e461a98178ca47eabce1802bc11fb8d3
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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