Reaktion #49219

Reaktionsgleichung

methylbutylamine

( 1 )

(2R,4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Methyl 3-(butyl(methyl)carbamoyl)benzoate

3-(methoxycarbonyl)benzoic acid

Hunig's base

HATU

→

title compound

3-(butyl(methyl)carbamoyl)benzoic acid

Lösungsmittel

dichloromethane

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas then added
2. 2
   workup.STIRRINGthe reaction mixture was stirred at rt for 3 h
3. 3
   SonstigeDichloromethane was removed
4. 4
   workup.ADDITIONethyl acetate (300 mL) was added
5. 5
   Waschenthe mixture was washed with 1N HCl, sodium carbonate solution, H2O
6. 6
   Sonstigedried
7. 7
   Einengenconcentrated

Vorschrift

Step F (1): Methyl 3-(butyl(methyl)carbamoyl)benzoate. To a solution of 3-(methoxycarbonyl)benzoic acid (1.8 g, 10 mmol) in dichloromethane (40 mL) and DMF (20 mL) was added Hunig's base (2.58 g, 20 mmol) to make a clear solution and HATU (4.18 g, 11 mmol) was then added. After stirring for 10 min, the reaction mixture was added methylbutylamine (1.13 g, 13 mmol) and the reaction mixture was stirred at rt for 3 h. Dichloromethane was removed and ethyl acetate (300 mL) was added and the mixture was washed with 1N HCl, sodium carbonate solution, H2O, dried and concentrated to give the title compound ready for next step without purification: 1H NMR (CDCl3, 500 MHz) δ 0.79-0.98 (3H, m), 1.15 (1H, m), 1.41 (1H, brd s), 1.52 (1H, brd s), 1.64 (1H, m), 2.92-3.07 (2H, m), 3.21 (1H, brd s), 3.53 (1H, brd s), 3.91 (3H, s), 7.47 (1H, m), 7.58 (1H, d, J=10 Hz), 8.05-8.07 (2H, m).

Quelle