Tributyltin Chloride → 1-[6-(Tributylstannyl)pyridin-2-yl]cyclobutanol
Reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2([OH:12])[CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[CH2:24]([Sn:28](Cl)([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH3:27].[Cl-].[NH4+]>O1CCCC1>[CH2:33]([Sn:28]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:29][CH2:30][CH2:31][CH3:32])[C:2]1[N:7]=[C:6]([C:8]2([OH:12])[CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1)[CH2:34][CH2:35][CH3:36]Participants
Procedure
Tetrahydrofuran (10 mL) solution of 293.1 mg of 1-(6-bromo-2-pyridinyl)cyclobutanol obtained in Example 69-1 was cooled to −78° C. in an acetone/dry ice bath in a nitrogen atmosphere, and 1.8 mL of 1.58 M n-butyllithium/hexane solution was gradually added thereto, and stirred for 30 minutes. Subsequently, tetrahydrofuran (2.0 mL) solution of 0.36 mL of tri-n-butyltin chloride was added thereto at −78° C., and the reaction solution was stirred for 30 minutes. This was processed with aqueous saturated ammonium chloride solution, extracted with ethyl acetate, and the organic layer was washed with saturated saline water, and purified through silica gel column chromatography (hexane/ethyl acetate) to obtain 48.7 mg of the entitled compound as a pale yellow oily substance.
Workup
- additionwas gradually added
- stirringat −78° C., and the reaction solution was stirred for 30 minutes
- extractionextracted with ethyl acetate
- washthe organic layer was washed with saturated saline water
- custompurified through silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-4465192bcbf9496eb3bab388664d9363
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791125B2
Reaction notes
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