Reaktion #2133403

Reaktionsgleichung

Sodium tert-butoxide

(R)-3,3-Dimethyl-2-aminobutane

2-(2-bromoethyl)-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester

potassium iodide

→

(R)-5-phenoxymethyl-2-[2-(1,2,2-trimethyl-propylamino)-ethyl]-2H-pyrazole-3-carboxylic acid

(R)-5-phenoxymethyl-2-[2-(1,2,2-trimethyl-propylamino)-ethyl]-2H-pyrazole-3-carboxylic acid ethyl ester

Lösungsmittel

DMF

ACN

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at 130° C. for 20 minutes under microwave irradiation
2. 2
   SonstigeThe solvent was evaporated in vacuo
3. 3
   WaschenThe crude product was washed with a 2N solution of HCl until pH 1
4. 4
   Extraktionextracted with AcOEt
5. 5
   SonstigeThe organic layer was separated
6. 6
   Trocknendried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Sonstigethe solvents evaporated in vacuo

Vorschrift

(R)-3,3-Dimethyl-2-aminobutane (0.37 g, 2.86 mmol) was added to a suspension of 2-(2-bromoethyl)-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (0.1 g, 0.28 mmol) and potassium iodide (9 mg, 0.056 mmol) in ACN (1 mL). The mixture was stirred at 90° C. for 20 hours. Sodium tert-butoxide (41 mg, 0.42 mmol) and DMF (1 mL) was added and the mixture was stirred at 130° C. for 20 minutes under microwave irradiation. The solvent was evaporated in vacuo. The crude product was washed with a 2N solution of HCl until pH 1 and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield a 1:1 mixture (R)-5-phenoxymethyl-2-[2-(1,2,2-trimethyl-propylamino)-ethyl]-2H-pyrazole-3-carboxylic acid ethyl ester and (R)-5-phenoxymethyl-2-[2-(1,2,2-trimethyl-propylamino)-ethyl]-2H-pyrazole-3-carboxylic acid (113 mg, 57%) as a yellow oil which was used in the next step without any further purification.

Quelle