Reaction #63232

ord-14c84d7a4a1b47bda48304e6557ddf00

Reaction equation

CN1C[C@@H](NC(=O)OCc2ccccc2)C[C@@H]2c3cccc4[nH]cc(c34)C[C@H]21
8α-benzyloxycarbonylamino-6-methylergoline
N#CBr
cyanobromide
→
N#CN1C[C@@H](NC(=O)OCc2ccccc2)C[C@@H]2c3cccc4[nH]cc(c34)C[C@H]21
8α-benzyloxycarbonylamino-6-cyanoergoline

Reactants

CN1C[C@@H](NC(=O)OCc2ccccc2)C[C@@H]2c3cccc4[nH]cc(c34)C[C@H]21
8α-benzyloxycarbonylamino-6-methylergoline
N#CBr
cyanobromide

Reagents

None

Solvents

ClC(Cl)Cl
chloroform

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationfinally concentrated on a rotary evaporator
  2. 2
    Otherto give the heading compound which
  3. 3
    Otheris dried in a high vacuum

Procedure

A solution of 29.5 g (79 mM) of 8α-benzyloxycarbonylamino-6-methylergoline obtained from step (a) and 25 g (236 mM) cyanobromide in 600 ml chloroform is stirred for 65 hours at room temperature and finally concentrated on a rotary evaporator to give the heading compound which is dried in a high vacuum.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04764517uspto-grants-1988_08