Ethyl Acetate → 5-Aminomethyl-2-(3-dipropylaminobutyl)-1-methoxymethoxy-indane

HRID 1174020Notes

Reaction equation

HRID 1174020 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([O:12][CH2:13][O:14][CH3:15])[CH:7]([CH2:16][CH2:17][CH:18]([N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])[CH3:19])[CH2:6]2)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1.CO>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([O:12][CH2:13][O:14][CH3:15])[CH:7]([CH2:16][CH2:17][CH:18]([N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])[CH3:19])[CH2:6]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 230792975-Cyano-2-(3-dipropylaminobutyl)-1-methoxymethoxy-indane

Product 1

HCID 230793035-Aminomethyl-2-(3-dipropylaminobutyl)-1-methoxymethoxy-indaneYield 42.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound (436.8 mg) obtained in Example 127-9 was dissolved in THF (21.8 ml) and added with lithium aluminum hydride (138.7 mg), followed by stirring at room temperature for 24 hours. The reaction solution was added with ethyl acetate, methanol, and a 10% aqueous potassium sodium tartrate solution, and stirred for 1 hour, followed by separation/extraction with chloroform. The extract was washed with saturated saline solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (189.7 mg) as a yellow oily substance.

Workup

  1. extractionfollowed by separation/extraction with chloroform
  2. washThe extract was washed with saturated saline solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationfollowed by concentration under reduced pressure
  5. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-86d6273831ad40a88d484de7b14631df
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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