Benzylamine → cis-8-Benzoyl-5-benzyl-2-oxa-5,8-diazabicyclo[4.3.0]nonane

HRID 374553

Reaction equation

HRID 374553 reaction equation
[C:1]([N:9]1[CH2:13][C@@H:12]([O:14][CH2:15][CH2:16]OS(C2C=CC(C)=CC=2)(=O)=O)[C@H:11](Br)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1(C)C(C)=CC=CC=1>[C:1]([N:9]1[CH2:13][C@@H:12]2[C@@H:11]([N:36]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:16][CH2:15][O:14]2)[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 86748810trans-1-Benzoyl-3-bromo-4-(2-tosyloxyethoxy)-pyrrolidine

Product 1

HCID 53682667cis-8-Benzoyl-5-benzyl-2-oxa-5,8-diazabicyclo[4.3.0]nonane

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

124 g (0.265 mol) of trans-1-benzoyl-3-bromo-4-(2-tosyloxyethoxy)-pyrrolidine are heated under reflux overnight in 1.5 1 of xylene together with 86 g 0.8 mol) of benzylamine. The salts of the benzylamine are filtered off with suction and the filtrate is concentrated.

Workup

  1. filtrationThe salts of the benzylamine are filtered off with suction
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-198d28caa75146abba072ad94f80ad82
Source dataset
uspto-grants-1996_01
Patent number
US05480879

Linked notes

Loading…