2-(Tributylstannyl)pyridine → (R)-3'-[4-(2-Pyridyl)thiophen-2-yl]spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one
반응식
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]=1참가 물질
3
실험 절차
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+).
후처리
- 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
출처 및 근거
- ORD 기록
- ord-3bd167d02be145a4bc85c38811c20389
- 출처 데이터셋
- uspto-grants-2009_04
- 특허 번호
- US07514567B2
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