Reaction #640540

Reaction equation

3-pyridylcarbinol

N,N′-disuccinimidyl carbonate

pyridine

→

N-Hydroxysuccinimide 3-pyridylmethyl carbonate

Yield 115.3%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Concentrationconcentrated in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
3. 3
   Washwashed with saturated sodium bicarbonate, brine
4. 4
   Dryingdried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated

Procedure

To a solution of 2.5 g (22.9 mmol) of 3-pyridylcarbinol in 100 mL of anhydrous acetonitrile was added 8.8 g (34.4 mmol) of N,N′-disuccinimidyl carbonate and 5.55 mL (68.7 mmol) of pyridine. The solution was stirred for 1 hour and then concentrated in vacuo. The residue was dissolved in ethyl acetate, then washed with saturated sodium bicarbonate, brine, dried over magnesium sulfate, filtered and concentrated to afford 5.3 g of N-Hydroxysuccinimide-3-pyridylmethyl carbonate, mass spectrum m/e=251 (M+H), which was used directly in the next step without purification.

Source