2-(Tri-n-butylstannyl)thiophene → HCID 11256496, compound

HRID 2109433Notes

Reaction equation

HRID 2109433 reaction equation
Br[C:2]1[S:6][C:5]([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])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)CCC>>[S:26]1[CH:27]=[CH:28][CH:29]=[C:25]1[C:2]1[S:6][C:5]([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])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 10132189HCID 10132189, compound

Product 1

HCID 11256496HCID 11256496, compound

Procedure

The title compound was prepared by a method analogous to that described in Example 4 from (R)-3′-(5-bromothiophen-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one and 2-(tri-n-butylstannyl)thiophene. The solid obtained from flash chromatography was further purified by reverse phase HPLC on a C18 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 an off-white solid (100 mg), m/z 347 (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 C18 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-09a3f241ce8248c6a8a06463cc16ce3d
Source dataset
uspto-grants-2009_04
Patent number
US07514567B2

Reaction notes

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