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

HRID 2109476Notes

Reaction equation

HRID 2109476 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[S:16][C:17]([N:20]2[CH:24]=[CH:23][CH:22]=[N:21]2)=[CH:18][CH:19]=1>[Cu]I>[N:21]1[N:20]([C:17]2[S: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][CH:18]=2)[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 5310971AR-R-17779HCID 125544912-Bromo-5-(2-pyrazolyl)thiophene

Product 1

HCID 69053746(R)-3'-[5-(2-Pyrazolyl)thiophen-2-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 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 2-bromo-5-(2-pyrazolyl)thiophene using 3.6 equivalents of copper (I) iodide. The title compound was obtained as a pale solid, m/z 343 (MH+).

Workup

  1. customThe compound was prepared by a method analog to

Sources & evidence

ORD record
ord-b5ff190ba9f44c26838766df9170ca2c
Source dataset
uspto-grants-2009_04
Patent number
US07514567B2

Reaction notes

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