Dimethylformamide → 3-(1,1-Dimethylethyl)-4-(1-pyrrolidinyl)benzaldehyde

HRID 1698404Notes

Reaction equation

HRID 1698404 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:3]=1.C([Li])CCC.CN([CH:25]=[O:26])C>>[C:13]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)[CH:25]=[O:26])([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 666722611-(4-Bromo-2-tert-butyl-phenyl)-pyrrolidineHCID 178418339Butyllithium

Product 1

HCID 860427013-(1,1-Dimethylethyl)-4-(1-pyrrolidinyl)benzaldehydeYield 80.1%

Procedure

In a manner analogous to example 1 d, the process is carried out by a reaction of 7.6 g (27 mmol) of 1-(4-bromo-2-tert-butylphenyl)pyrrolidine with 16.2 ml (40 mmol) of a 2.5M solution of n-butyllithium and 3.1 ml (40 mmol) of DMF. 5 g of 3-tert-butyl-4-pyrrolidin-1-ylbenzaldehyde are obtained in the form of a yellow oil (yield=80%).

Workup

  1. customanalogous to example 1 d

Sources & evidence

ORD record
ord-72dcd5a6e084408da655188da285cbb5
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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