(3R*,4S*)-N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo[2.2.2]octane-3-carboxamide → (3R*,4S*)-N,N-Diethyl-6-diphenylmethyl-5-oxo-1-azabicyclo[2.2.2]octane-3-carboxamide

HRID 862119Notes

Reaction equation

HRID 862119 reaction equation
[CH2:1]([N:3]([CH2:31][CH3:32])[C:4]([C@@H:6]1[C@@H:11]2[CH2:12][CH2:13][N:8]([CH:9]([CH:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:10]32OCC[O:14]3)[CH2:7]1)=[O:5])[CH3:2]>Cl>[CH2:31]([N:3]([CH2:1][CH3:2])[C:4]([C@@H:6]1[C@@H:11]2[CH2:12][CH2:13][N:8]([CH:9]([CH:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:10]2=[O:14])[CH2:7]1)=[O:5])[CH3:32]

Participants

3

Reactant 1

HCID 53633467(3R*,4S*)-N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo[2.2.2]octane-3-carboxamide

Product 1

HCID 53867570(3R*,4S*)-N,N-Diethyl-6-diphenylmethyl-5-oxo-1-azabicyclo[2.2.2]octane-3-carboxamideYield 68%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 22 (6.5 g, 15 mmol) in 6N-HCl aq (100 ml) was heated at reflux for 10 hours. The resulting solution of sodium hydroxide (NaOH) (24 g) in water (100 ml) and extracted with CH2Cl2 (100 ml) four times. The combined extracts were dried over Na2SO4 and concentrated. The clude was purified by recrystallization from EtOH to give 23 (1:1 mixture at 6-position; 10 mmol, 68%).

Workup

  1. temperatureat reflux for 10 hours
  2. extractionThe resulting solution of sodium hydroxide (NaOH) (24 g) in water (100 ml) and extracted with CH2Cl2 (100 ml) four times
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe clude was purified by recrystallization from EtOH

Sources & evidence

ORD record
ord-d5915e0dd7084e82aef85dccda6608d2
Source dataset
uspto-grants-1998_02
Patent number
US05716965

Reaction notes

Loading…