Reaction #452458

Reaction equation

H2O

product

Boc-4-aminomethylbicyclo-[2.2.2]octane carboxamide

(methoxycarbonylsulfamoyl)-triethylammonium hydroxide

CHCl3 CH3OH-H2O

→

Boc-4-aminomethylbicyclo-[2.2.2]octane nitrile

Solvents

—

1-g

CH2Cl2

pyridine

Conditions

Workup

1. 1
   Otherthe solution was evaporated
2. 2
   Otherto give a paste
3. 3
   workup.STIRRINGstirring
4. 4
   Otherto afford
5. 5
   workup.WAITafter standing 20 hr at 0° C.
6. 6
   Filtrationfiltration
7. 7
   Otherdrying in vacuo

Procedure

A solution of 7.52 g (26.6 mmol) of the product from step C in 50 ml of CH2Cl2 and 80 ml of anhydrous pyridine was treated with 11.12 g of (methoxycarbonylsulfamoyl)-triethylammonium hydroxide inner salt (Burgess reagent) in 1-g portions over 5 min. After stirring for 1.5 hr, TLC (90-10-1, CHCl3 -CH3OH-H2O) showed complete conversion to product, and the solution was evaporated to give a paste, to which H2O was added, up to 400 ml, with trituration and stirring to afford, after standing 20 hr at 0° C., filtration and drying in vacuo, the title compound as a white solid.

Source