Tetrahydrofuran → 2-[3,3-Diphenyl-3-(pyridin-2-yl)propyl]-2-azabicyclo[2.2.2]octane

HRID 1973692Notes

Reaction equation

HRID 1973692 reaction equation
C1([C:7]2[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=2[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)C=CC=CC=1.[CH2:20]([Li])[CH2:21][CH2:22][CH3:23].Cl[CH2:26][CH2:27][N:28]1[CH2:33][CH:32]2[CH2:34][CH2:35][CH:29]1[CH2:30][CH2:31]2.O1CC[CH2:38][CH2:37]1>>[C:20]1([C:9]([C:8]2[CH:7]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH2:26][CH2:27][N:28]2[CH2:33][CH:32]3[CH2:34][CH2:35][CH:29]2[CH2:30][CH2:31]3)[CH:38]=[CH:37][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 126123252-(2-Chloroethyl)-2-azabicyclo[2.2.2]octaneHCID 543881562-(2-Phenylbenzyl) pyridineHCID 178418339Butyllithium

Product 1

HCID 203569032-[3,3-Diphenyl-3-(pyridin-2-yl)propyl]-2-azabicyclo[2.2.2]octane

Procedure

This method represents a modification of methods described by Martensson and Nilson, Acta Chem. Scand. 19 (3), 711-12 (1965) -- CA-63-6968h. Thus, 1 part of 2-(2-phenylbenzyl) pyridine is reacted with 1 part of n-Butyl lithium in tetrahydrofuran at -70° C. and then reacted with 1 part of 2-(2-chloroethyl)-2-azabicyclo[2.2.2 ]octane to provide 2-[3,3-diphenyl-3-(2-pyridyl)propyl]-2-azabicyclo[2.2.2 ]octane.

Workup

  1. customCA-63-6968h

Sources & evidence

ORD record
ord-6c4a2b04735e4f758cd558d332e4bcc1
Source dataset
uspto-grants-1976_12
Patent number
US03998832

Reaction notes

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