Diisopropylethylamine → n-Trimethylsilylethoxycarbonyl-1,2-diaminoethanehydrochloride

Temperature

0 °C

N-(t-Butyloxycarbonyl)-1,2-diaminoethane (8.0 g, 50 mmol) is dissolved in THF (200 mL), diisopropylethylamine (6.5 g, 50 mmol) is added and the solution cooled to 0° C. To this cold solution is added dropwise trimethylsilylethoxycarbonylchloride (9.0 g, 50 mmol) over 10 minutes. After stirring an additional 30 minutes the reaction is filtered and the filtrate is evaporated to an oil. This oil is dissolved in 100 mL of diethyl ether and washed with dilute HCl solution (3×25 mL), dried, filtered and evaporated to give an oil. The oil is dissolved in 100 mL of dichloromethane and dry HCl gas is bubbled through the solution for 30 minutes and the reaction stirred for 1 hour. The reaction is diluted with 200 mL of cold diethyl ether and allowed to stand at -5° C. for 12 hours. The colorless solid formed is collected and stored protected from moisture.

1. filtrationis filtered
2. customthe filtrate is evaporated to an oil
3. dissolutionThis oil is dissolved in 100 mL of diethyl ether
4. washwashed with dilute HCl solution (3×25 mL)
5. customdried
6. filtrationfiltered
7. customevaporated
8. customto give an oil
9. customdry HCl gas is bubbled through the solution for 30 minutes
10. stirringthe reaction stirred for 1 hour
11. additionThe reaction is diluted with 200 mL of cold diethyl ether
12. waitto stand at -5° C. for 12 hours
13. customThe colorless solid formed
14. customis collected

ORD record

ord-71f9fd10854a4b8bb1c63b4acc0d0f21

Source dataset

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05831014