Ethanol → 3-(4-Iodo-1H-pyrazol-1-yl)cyclobutanol

HRID 1947845Notes

Reaction equation

HRID 1947845 reaction equation
[I:1][C:2]1[CH:3]=[N:4][N:5]([CH:7]2[CH2:10][C:9](=[O:11])[CH2:8]2)[CH:6]=1.[BH4-].[Na+].C(O)C>>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH:7]2[CH2:8][CH:9]([OH:11])[CH2:10]2)[CH:6]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 672547783-(4-iodo-1H-pyrazol-1-yl)cyclobutan-1-one2×

Product 1

HCID 672540253-(4-Iodo-1H-pyrazol-1-yl)cyclobutanolYield 94.9%

Conditions

Temperature
0 °C

Procedure

3-(4-Iodo-pyrazol-1-yl)cyclobutanone (Compound 100D, 1.000 g, 3.816 mmol), sodium borohydride (145.8 mg, 3.854 mmol) and ethanol (22.28 mL, 381.6 mmol) were added to a round bottom flask and the reaction mixture was stirred at 0° C. for 3 h. Reaction mixture was concentrated in vacuo and washed with water extracting with DCM. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo to afford 956 mg of the final compound as colorless oil. Compound was taken on to the next step without further purification. MS (ES+): m/z 264.86 (100) [MH+]; HPLC: tR=2.50 min (Polar—5 min, ZQ3).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo
  3. washwashed with water extracting with DCM
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-977aacb31ea94dc8acae4170c264933e
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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