Water → (1-(4-nitro-1H-pyrazol-1-yl)cyclopropyl)methanol

HRID 714841Notes

Reaction equation

HRID 714841 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([C:9]2([C:12](OC)=[O:13])[CH2:11][CH2:10]2)[CH:8]=1)([O-:3])=[O:2].[BH4-].[Li+].O>O1CCCC1>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([C:9]2([CH2:12][OH:13])[CH2:10][CH2:11]2)[CH:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 117839997Methyl 1-(4-nitro-1H-pyrazol-1-YL)cyclopropane-1-carboxylate

Product 1

HCID 91619134(1-(4-nitro-1H-pyrazol-1-yl)cyclopropyl)methanolYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-(4-nitro-1H-pyrazol-1-yl)cyclopropanecarboxylate (1.0 g) obtained in Step A of Example 128 in tetrahydrofuran (50 mL) was added lithium tetrahydroborate (160 mg), and the mixture was stirred at room temperature for 10 hr. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (620 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-eb94f5acd9c94c659995c30e02a71918
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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