Ethanol → 3-(4-Iodo-1H-pyrazol-1-yl)cyclobutanol
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]=1Participants
4
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
- customReaction mixture
- concentrationwas concentrated in vacuo
- washwashed with water extracting with DCM
- dry with materialThe organic layer was dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-669eb04e50fd463a84a95853cab1bf27
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096624B2
Reaction notes
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