2-(Tributylstannyl)pyridine → (R)-3'-[4-(2-Pyridyl)thiophen-2-yl]spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one
反応式
Br[C:2]1[CH:3]=[C:4]([N:7]2[CH2:11][C@:10]3([CH:16]4[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]4)[CH2:12]3)[O:9][C:8]2=[O:19])[S:5][CH:6]=1.C([Sn](CCCC)(CCCC)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)CCC>>[N:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:2]1[CH:3]=[C:4]([N:7]2[CH2:11][C@:10]3([CH:16]4[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]4)[CH2:12]3)[O:9][C:8]2=[O:19])[S:5][CH:6]=1参加物
3
実験手順
The title compound was prepared by a method analogous to that described in Example 5 from (R)-3′-(4-bromothiophen-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one and 2-(tri-n-butylstannyl)pyridine. The solid obtained from flash chromatography was further purified by reverse phase HPLC on a Polar reverse phase column using a gradient of 5-45% acetonitrile/water (each solvent containing 0.1% trifluoroacetic acid as a buffer) as the eluant. The product-containing fractions were evaporated. The residue was partitioned between saturated aqueous potassium carbonate and chloroform and the chloroform layer was dried (magnesium sulfate), filtered and evaporated to give the title compound as a pale solid, m/z 342 (MH+).
後処理
- customThe title compound was prepared by a method analogous to
- customThe solid obtained from flash chromatography
- customwas further purified by reverse phase HPLC on a Polar reverse phase column
- additioncontaining 0.1% trifluoroacetic acid as a buffer) as the eluant
- customThe product-containing fractions were evaporated
- customThe residue was partitioned between saturated aqueous potassium carbonate and chloroform
- dry with materialthe chloroform layer was dried (magnesium sulfate)
- filtrationfiltered
- customevaporated
出典と根拠
- ORDレコード
- ord-3bd167d02be145a4bc85c38811c20389
- 出典データセット
- uspto-grants-2009_04
- 特許番号
- US07514567B2
反応ノート
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