2-(Tributylstannyl)pyridine → (R)-3'-[4-(2-Pyridyl)thiophen-2-yl]spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one

HRID 2109442Notes

Reaction equation

HRID 2109442 reaction equation
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

Participants

3

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 57634260(R)-3'-(4-Bromothiophen-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one

Product 1

HCID 57634266(R)-3'-[4-(2-Pyridyl)thiophen-2-yl]spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one

Procedure

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+).

Workup

  1. customThe title compound was prepared by a method analogous to
  2. customThe solid obtained from flash chromatography
  3. customwas further purified by reverse phase HPLC on a Polar reverse phase column
  4. additioncontaining 0.1% trifluoroacetic acid as a buffer) as the eluant
  5. customThe product-containing fractions were evaporated
  6. customThe residue was partitioned between saturated aqueous potassium carbonate and chloroform
  7. dry with materialthe chloroform layer was dried (magnesium sulfate)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-3bd167d02be145a4bc85c38811c20389
Source dataset
uspto-grants-2009_04
Patent number
US07514567B2

Reaction notes

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