Reaction #10049

Reaction equation

Triethylamine

methyl-3-(aminomethyl)-2-(methoxycarbonyl)benzoate hydrochloride

Cyclopropylcarbonyl chloride

→

product

Yield 103.0%

Methyl-3-[(cyclopropylcarbonylamino)methyl]-2-(methoxycarbonyl)benzoate

Yield 103.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.ADDITIONAfter addition
2. 2
   Temperaturewarmed to room temperature for 2 hours
3. 3
   WashThe mixture was washed with water (2×30 ml), brine (30 ml)
4. 4
   Otherdried
5. 5
   OtherSolvent was removed in vacuo
6. 6
   Otherthe product was purified by flash chromatography (dichloromethane/ethyl acetate 9 to 1)

Procedure

Triethylamine (1.87 g, 18 mmol) was added dropwise to a stirred suspension of methyl-3-(aminomethyl)-2-(methoxycarbonyl)benzoate hydrochloride (2.0 g, 7 mmol) in dichloromethane (40 ml). The mixture was cooled in an ice bath to 4° C. Cyclopropylcarbonyl chloride (0.99 g, 9 mmol) was added slowly at 4–8° C. After addition, the mixture was stirred in ice bath for 30 min and then warmed to room temperature for 2 hours. The mixture was washed with water (2×30 ml), brine (30 ml) and dried. Solvent was removed in vacuo and the product was purified by flash chromatography (dichloromethane/ethyl acetate 9 to 1) to give 2.1 g (93%) of the product as a white solid: 1H NMR (CDCl3) (7.87 (d, J=7.8 Hz, 1H), 7.63 (d, J=7.7 Hz, 1H), 7.46 (t, J=7.77 Hz, 1H), 6.31 (m, 1H), 4.43 (d, J=6.0 Hz, 2H), 3.95 (s, 3H), 3.90 (s, 3H), 1.36–1.29 (m, 1H), 0.99–0.93 (m, 2H), 0.76–0.69 (m, 2H).

Source