Reaktion #1780190

Reaktionsgleichung

water

(3R)-(+)-3-Boc-aminopyrrolidine

triethylamine

DMF

2-(4-chloro-7-methylquinazolin-2-yl)phenol

DMF

→

tert-butyl (R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate

Ausbeute 55.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe aqueous layer was extracted with dichloromethane (3×300 mL)
2. 2
   Waschenthe combined organic layers were washed with saturated aqueous NaCl solution (300 mL)
3. 3
   Trocknendried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated to dryness under reduced pressure
6. 6
   workup.ADDITIONThe yellow residue (21 g) was treated with 100 mL methanol at room temperature
7. 7
   FiltrationThe solid was collected by filtration
8. 8
   Waschenwas washed with methanol

Vorschrift

To a cooled (0-5° C.) solution of (3R)-(+)-3-Boc-aminopyrrolidine (12.0 g, 65 mmol) and triethylamine (19 mL, 129 mmol) in DMF (100 mL) was added a solution of 2-(4-chloro-7-methylquinazolin-2-yl)phenol (17.4 g, 64 mmol) in CH2Cl2 (500 mL) and DMF (100 mL). After stirring the mixture for 5 hours at room temperature, water (900 mL) was added. The aqueous layer was extracted with dichloromethane (3×300 mL), and the combined organic layers were washed with saturated aqueous NaCl solution (300 mL), dried over sodium sulfate, filtered, and evaporated to dryness under reduced pressure. The yellow residue (21 g) was treated with 100 mL methanol at room temperature. The solid was collected by filtration and was washed with methanol to yield tert-butyl (R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate (15.1 g, 55%) as a yellow solid.

Quelle