Water → N-(p-toluenesulfonyl)-3-(aminoethyl)-4-(bromomethyl)-3-pyrroline

HRID 1534812Notes

Reaction equation

HRID 1534812 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:14][C:13]([CH2:15][C:16]#[N:17])=[C:12]([CH2:18][Br:19])[CH2:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[C:1]1([CH3:20])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH2:11][C:12]([CH2:18][Br:19])=[C:13]([CH2:15][CH2:16][NH2:17])[CH2:14]2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 19908246N-(p-toluenesulfonyl)-3-(bromomethyl)4-(cyanomethyl)-3-pyrrolineHCID 21226445Aluminium lithium hydride

Product 1

HCID 54170899N-(p-toluenesulfonyl)-3-(aminoethyl)-4-(bromomethyl)-3-pyrrolineYield 49.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

4 g of N-(p-toluenesulfonyl)-3-(bromomethyl)-4-(cyanomethyl)-3-pyrroline, prepared in Preparation 6, was dissolved in 100 ml of ethyl ether. The solution was slowly added to the suspension of 1 g of lithium aluminum hydride (LAH) in 20 ml of ethyl ether, and heated with refluxing for 3 hours. The reaction mixture was cooled by ice water. After adding 3 ml of water, it was stirred for 30 minutes and filtered off. The filtrate was concentrated. 2 g of the title compound was obtained (yield 49%).

Workup

  1. temperatureheated
  2. temperaturewith refluxing for 3 hours
  3. filtrationfiltered off
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3bff72904e444764a88b926b3bc8c90c
Source dataset
uspto-grants-1992_02
Patent number
US05091384

Reaction notes

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