Reaction #1797518

Reaction equation

Sodium cyanoborohydride

4-(3-(4-tert-butylphenyl)-2-oxoimidazolidin-1-yl)benzaldehyde

acetic acid

azetidine-3-carboxylic acid

→

title product

Yield 10.0%

1-(4-(3-(4-tert-Butylphenyl)-2-oxoimidazolidin-1-yl)benzyl)azetidine-3-carboxylic acid

Yield 10.0%

Solvents

dimethylsulfoxide

dichloromethane MeOH

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction mixture was stirred for 6 hour at room temperature
2. 2
   Filtrationfiltered
3. 3
   Otherpurified by reverse phase preparative HPLC (Phenomenex

Procedure

A mixture of 4-(3-(4-tert-butylphenyl)-2-oxoimidazolidin-1-yl)benzaldehyde (32 mg, 0.1 mmol), acetic acid (50 μl) and azetidine-3-carboxylic acid (13 mg, 0.13 mmol) in dichloromethane/MeOH (1:1, 5 mL) was stirred at room temperature for 1 hour. Sodium cyanoborohydride (3.5 mg, 0.05 mmol) was added and the reaction mixture was stirred for 6 hour at room temperature. After concentration of solvent under reduced pressure, the resulting residue was dissolved in dimethylsulfoxide, filtered and purified by reverse phase preparative HPLC (Phenomenex reverse phase Luna 5u C18(2) column, 60×21.2 mm ID, mobile phase: A=0.05% TFA in water; B=0.05% TFA in acetonitrile. The flow rate was 10-12 mL/min) to yield the title product 4 mg (10%): 1H NMR (400 MHz, CDOD3) δ 7.72 (d, 2H), 7.51-7.40 (m, 6H), 4.33 (s, 2H), 4.28 (m, 4H), 4.02 (s, 4H), 3.64 (m, 1H), 1.32 (s, 9H). MS (ESI) m/z: Calculated: 407.22; Observed: 408.00 (M++1).

Source