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

HRID 1648479Notes

Reaction equation

HRID 1648479 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 with 86 g (0.3 mol) of benzylamine in 1.5 l of xylene under reflux overnight. The salts of the benzylamine are filtered off with suction, and the filtrate is concentrated.

Workup

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

Sources & evidence

ORD record
ord-f7118a019860452588c7bb504451d752
Source dataset
uspto-grants-1995_07
Patent number
US05436334

Reaction notes

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