Water → HCID 39871991, compound

HRID 2061640Notes

Reaction equation

HRID 2061640 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([S:13]([C:16]2([C:21]#[N:22])[CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>O1CCCC1>[C:7]1([S:13]([C:16]2([CH2:21][NH2:22])[CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:14])=[O:15])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 1204325HCID 1204325, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 39871991HCID 39871991, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

194 mg (5.1 mmol) of lithium aluminum hydride is added to a solution of 1 g (4.2 mmol) of 1-benzenesulfonyl-cyclopentanecarbonitrile in 20 ml of tetrahydrofuran. The reaction mixture is stirred at room temperature (RT) for 20 h. It is then hydrolyzed with 194 μl of water, 194 μl of a 15% soda solution and then 582 μl of water, stirred for 5 minutes, then filtered. The filtrate is evaporated and the residue is chromatographed on silica gel (dichloromethane then dichloromethane/methanol, 90/10, v/v). 420 mg of C-(1-benzenesulfonyl-cyclopentyl)-methylamine is obtained in the form of a colorless oil. (Yield=42%).

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated
  3. customthe residue is chromatographed on silica gel (dichloromethane

Sources & evidence

ORD record
ord-baf07bf649d04882a80a58c63eef31d5
Source dataset
uspto-grants-2012_10
Patent number
US08283378B2

Reaction notes

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