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

HRID 2080737Notes

Reaction equation

HRID 2080737 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 43%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound (436 mg) obtained in Example 11-9 was dissolved in THF (21.8 ml) and added with lithium aluminum hydride (138.7 mg) and the whole was stirred at room temperature for 24 hours. The reaction solution was added with ethyl acetate, methanol, and a 10% aqueous potassium sodium tartrate solution, and the whole was stirred for 1 hour, followed by extraction with chloroform. The extract was washed with a saturated saline solution and then 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 extraction with chloroform
  2. washThe extract was washed with a 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-58cccafe73214123929eba88514ec334
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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