Lithium triethylborohydride → (+/-)-6-(3-iodo-1-isopropyl-1H-pyrazol-5-yl)bicyclo[3.1.0]hexan-2-ol
Reaction equation
[I:1][C:2]1[CH:6]=[C:5]([CH:7]2[CH:13]3[CH:8]2[CH2:9][CH:10]2[CH:12]3[O:11]2)[N:4]([CH:14]([CH3:16])[CH3:15])[N:3]=1.[Li+].[B-](CC)(CC)CC>O1CCCC1.[Cl-].[NH4+]>[I:1][C:2]1[CH:6]=[C:5]([CH:7]2[CH:13]3[CH:8]2[CH2:9][CH2:10][CH:12]3[OH:11])[N:4]([CH:14]([CH3:16])[CH3:15])[N:3]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
To an ice-cooled solution of 3-iodo-1-isopropyl-5-(3-oxatricyclo[4.1.0.02,4]heptan-7-yl)-1H-pyrazole (0.500 g, 1.52 mmol) in anhydrous tetrahydrofuran (5 mL) was added lithium triethylhydroborate (10 mL, 1 M in THF) dropwise. The reaction mixture was warmed to 20° C. After 1 h, the reaction mixture was cooled to 0° C. and diluted with saturated aqueous ammonium chloride solution (10 mL). The resulting mixture was extracted with ethyl acetate (2×10 mL). The collected organic was concentrated in vacuo. Purification by flash column chromatography (17% ethyl acetate in petroleum ether) afforded product as a colorless oil (460 mg, 91% yield).
Workup
- temperaturethe reaction mixture was cooled to 0° C.
- extractionThe resulting mixture was extracted with ethyl acetate (2×10 mL)
- concentrationThe collected organic was concentrated in vacuo
- customPurification by flash column chromatography (17% ethyl acetate in petroleum ether)
Sources & evidence
- ORD record
- ord-34577d437b374722a1266d9108540edb
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365583B2
Reaction notes
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