Borane;tetrahydrofuran → [3-Iodo-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]-methanol

HRID 526766Notes

Reaction equation

HRID 526766 reaction equation
[I:1][C:2]1[C:6]([C:7](O)=[O:8])=[CH:5][N:4]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[N:3]=1.B.C1COCC1>CC(=O)OCC>[I:1][C:2]1[C:6]([CH2:7][OH:8])=[CH:5][N:4]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[N:3]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 904248953-Iodo-1-(tetrahydro-pyran-2-yl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 90424555[3-Iodo-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]-methanolYield 83.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carboxylic acid (34 g, 105 mmol) in BH3-THF (340 mL, 340 mmol, 1M in THF) was stirred at rt overnight. Solvent was evaporated under vacuum and the residue dissolved in DCM (340 mL), washed with water (340 mL×3), dried and concentrated. The residue was purified by SGC using Hex: EA (0%-70%) as eluent to afford (3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methanol (27 g, yield: 83%). LCMS (method C): RT=1.74 min, m/z=309.1 [M+H]+.

Workup

  1. customSolvent was evaporated under vacuum
  2. dissolutionthe residue dissolved in DCM (340 mL)
  3. washwashed with water (340 mL×3)
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by SGC

Sources & evidence

ORD record
ord-09d32dd271d94ac29f9ab4c17ba5adf6
Source dataset
uspto-grants-2016_05
Patent number
US09346761B2

Reaction notes

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