tert-Butyl acrylate → tert-butyl N-[3-(4-hydroxyphenyl)propyl]-beta-alaninate

HRID 1169630Notes

Reaction equation

HRID 1169630 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH:13]=[CH2:14]>CO>[OH:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][CH2:2][NH:1][CH2:14][CH2:13][C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 15458tert-Butyl acrylateHCID 4574248HCID 4574248, compound

Product 1

HCID 23121488tert-butyl N-[3-(4-hydroxyphenyl)propyl]-beta-alaninate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol solution (25 mL) of 4-(3-aminopropyl)phenol (1.83 g), tert-butyl acrylate (1.7 mL) was added dropwise thereto at room temperature, followed by stirring at room temperature overnight. The reaction mixture was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate→ethyl acetate:methanol=3:1) to give the title compound (1.55 g) having the following physical properties. TLC: Rf 0.24 (ethyl acetate:methanol 5:1);

Workup

  1. customat room temperature
  2. concentrationThe reaction mixture was concentrated
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate→ethyl acetate:methanol=3:1)

Sources & evidence

ORD record
ord-0fab8896541841cc802419e13b1774b8
Source dataset
uspto-grants-2010_11
Patent number
US07825109B2

Reaction notes

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