Cyanogen Bromide → 8alpha-Benzyloxycarbonylamino-6-cyanoergoline

HRID 34954Notes

Reaction equation

HRID 34954 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:26][C@H:25]2[C@@H:15]([CH2:16][C:17]3[C:27]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]2=4)[NH:19][CH:18]=3)[N:14]([CH3:28])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)#[N:30]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:26][C@H:25]2[C@@H:15]([CH2:16][C:17]3[C:27]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]2=4)[NH:19][CH:18]=3)[N:14]([C:28]#[N:30])[CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 704178488alpha-Benzyloxycarbonylamino-6-methylergoline

Product 1

HCID 867423318alpha-Benzyloxycarbonylamino-6-cyanoergoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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.

Workup

  1. concentrationfinally concentrated on a rotary evaporator
  2. customto give the heading compound which
  3. customis dried in a high vacuum

Sources & evidence

ORD record
ord-14c84d7a4a1b47bda48304e6557ddf00
Source dataset
uspto-grants-1988_08
Patent number
US04764517

Reaction notes

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