Acetic Acid → n-3-(4-Methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine

HRID 2215185Notes

Reaction equation

HRID 2215185 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:17][O:18][C:19]1[CH:29]=[CH:28][C:22]([O:23][CH2:24][CH2:25][CH2:26][NH2:27])=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>ClCCCl>[CH3:17][O:18][C:19]1[CH:29]=[CH:28][C:22]([O:23][CH2:24][CH2:25][CH2:26][NH:27][CH2:12][C:11]2[CH:14]=[CH:15][CH:16]=[C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:10]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 31521093-(4-Methoxy-phenoxy)-propylamineHCID 5049666Sodium triacetoxyborohydrideHCID 112071113-(t-Butyldimethylsilyloxy)benzaldehyde

Product 1

HCID 21949684n-3-(4-Methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-tert-Butyldimethylsilyloxybenzaldehyde (1.5 g, 6.34 mmol) was dissolved in 1,2-dichloroethane (10.0 mL). Subsequently, 3-(4-methoxyphenoxy)propylamine (1.5 g, 8.25 mmol) was added thereto, and the resultant mixture was stirred for 20 minutes. At room temperature, sodium triacetoxyborohydride (1.75 g, 8.25 mmol) and acetic acid (495 mg, 8.25 mmol) were added thereto, and the mixture was stirred overnight. A saturated aqueous sodium hydrogencarbonate solution was added thereto. The reaction mixture was extracted with chloroform, and the organic layer was washed with brine. The resultant mixture was subjected to drying over anhydrous sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=50/1), whereby the target compound was obtained (1.9 g, 78%).

Workup

  1. extractionThe reaction mixture was extracted with chloroform
  2. washthe organic layer was washed with brine
  3. dry with materialto drying over anhydrous sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=50/1), whereby the target compound
  4. customwas obtained (1.9 g, 78%)

Sources & evidence

ORD record
ord-7f098fe88f794398ab39f0b56bf9ff9a
Source dataset
uspto-grants-2006_09
Patent number
US07109226B2

Reaction notes

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