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

HRID 2109464Notes

Reaction equation

HRID 2109464 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:19]=[C:18]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[O:17][CH:16]=1>[Cu]I>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:18]2[O:17][CH:16]=[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:19]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 5310971AR-R-17779HCID 576342343-(4-Bromofuran-2-yl)pyridine

Product 1

HCID 11404592(R)-3'-[2-(3-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 analog to that described in Preparation 3 from (S)-spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one and 3-bromo-5-(3-pyridyl)-furan with 3 equivalents of copper (I) iodide. The title compound (119 mg) was obtained as a pale yellow solid, m/z 342 (MH+).

Workup

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

Sources & evidence

ORD record
ord-a20ca1816ddf46d2b92d9e43ed6482e5
Source dataset
uspto-grants-2009_04
Patent number
US07514567B2

Reaction notes

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