Water → 1-(4-Nitro-1H-pyrazol-1-yl)cyclobutanemethanol

HRID 714837Notes

Reaction equation

HRID 714837 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([C:9]2([C:13](OCC)=[O:14])[CH2:12][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([CH2:13][OH:14])[CH2:12][CH2:11][CH2:10]2)[CH:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 117840093ethyl 1-(4-nitro-1H-pyrazol-1-yl)cyclobutanecarboxylate

Product 1

HCID 1178406451-(4-Nitro-1H-pyrazol-1-yl)cyclobutanemethanolYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-(4-nitro-1H-pyrazol-1-yl)cyclobutanecarboxylate (500 mg) obtained in Step A of Example 127 in tetrahydrofuran (30 mL) was added lithium tetrahydroborate (68 mg), and the mixture was stirred at room temperature for 3 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 (410 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-6ac954b88e9645e98da983b2224c48c9
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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