Diethyl Ether → HCID 18510453, compound

HRID 1370686Notes

Reaction equation

HRID 1370686 reaction equation
[N:1]12[CH2:8][CH2:7][N:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[Br:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(OCC)(=O)C.C(OCC)C>CN(C)C(=O)C>[Br-:9].[C:14]([O:13][C:11]([CH2:10][N+:1]12[CH2:8][CH2:7][N:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 9237DabcoHCID 79177tert-Butyl bromoacetate

Product 1

HCID 18510453HCID 18510453, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To an ice-cold solution of 5.61 g of 1,4-diaza-bicyclo[2.2.2]octane in 50 ml of N,N-dimethylacetamide were added 7.33 ml of tert-butyl 2-bromo-acetate. The solution was stirred for 4 h at 20° and then, 0.5 l of ethyl acetate and 0.3 l of diethyl ether were added. The precipitate formed was isolated by filtration, washed thoroughly with 0.5 l of ethyl acetate and dried to give 14.7 g of 1-tert-butoxycarbonylmethyl-4-aza-1-azonia-bicyclo[2.2.2]octane bromide as white crystals.

Workup

  1. customThe precipitate formed
  2. customwas isolated by filtration
  3. washwashed thoroughly with 0.5 l of ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-26782fab6abd44d5b4e0f1b910b6205f
Source dataset
uspto-grants-2003_06
Patent number
US06583133B1

Reaction notes

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