AR-R-17779 → (R)-3'-[2-(4-Pyridyl)furan-4-yl]spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one

HRID 2109462Notes

Reaction equation

HRID 2109462 reaction equation
[O:1]1[C@@:5]2([CH:10]3[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]3)[CH2:6]2)[CH2:4][NH:3][C:2]1=[O:13].Br[C:15]1[CH:16]=[C:17]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[O:18][CH:19]=1>[Cu]I>[N:23]1[CH:22]=[CH:21][C:20]([C:17]2[O:18][CH:19]=[C:15]([N:3]3[CH2:4][C@:5]4([CH:10]5[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]5)[CH2:6]4)[O:1][C:2]3=[O:13])[CH:16]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 5310971AR-R-17779HCID 576342534-(4-Bromofuran-2-yl)pyridine

Product 1

HCID 11232593(R)-3'-[2-(4-Pyridyl)furan-4-yl]spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

The title compound was prepared by a method analogous to that described in Preparation 3 from (S)-spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one and 4-bromo-2-(4-pyridyl)furan using 4 equivalents of copper (I) iodide. The title compound (124 mg) was obtained as a pale yellow solid, m/z 342 (MH+).

Workup

  1. customThe title compound was prepared by a method analogous to

Sources & evidence

ORD record
ord-256ae9b81c8e4b7ba09f8dfffa1e4144
Source dataset
uspto-grants-2009_04
Patent number
US07514567B2

Reaction notes

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