Reaktion #1463189

Reaktionsgleichung

p-toluenesulfonyl chloride

tert-butyl N-(2-hydroxyethyl)carbamate

triethylamine

trimethylammonium chloride

iso-hexane

→

title compound

Ausbeute 66.1%

2-(tert-Butyloxycarbonylamino)ethyl tosylate

Ausbeute 66.1%

Lösungsmittel

ethyl acetate

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthen filtered
2. 2
   Waschenwashing with dichloromethane (100 mL)
3. 3
   WaschenThe filtrate was washed with 10% citric acid (3×100 mL) and brine (100 mL)
4. 4
   TrocknenThe organic layer was dried with magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   EinengenThe filtrate was concentrated under reduced pressure
7. 7
   Sonstigeto give an oil
8. 8
   workup.STIRRINGThe resultant slurry was stirred at room temperature for 17 hours
9. 9
   Filtrationfiltered
10. 10
    WaschenThe collected solid was washed with iso-hexane (240 mL)

Vorschrift

A solution of p-toluenesulfonyl chloride (28.40 g, 148 mmol) in dichloromethane (100 mL) was added dropwise over 30 minutes at 0° C. to a mixture of tert-butyl N-(2-hydroxyethyl)carbamate (20 g, 120 mmol), triethylamine (18.80 g, 186 mmol) and trimethylammonium chloride (1.18 g, 12.4 mmol) in dichloromethane (120 mL). The mixture was stirred at 0° C. for 1 hour then filtered, washing with dichloromethane (100 mL). The filtrate was washed with 10% citric acid (3×100 mL) and brine (100 mL). The organic layer was dried with magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure to give an oil. The oil was dissolved in ethyl acetate (40 mL) and then iso-hexane (160 mL) was added slowly. The resultant slurry was stirred at room temperature for 17 hours and then filtered. The collected solid was washed with iso-hexane (240 mL) to yield the title compound as a colourless powder (25 g, 64%).

Quelle