(1S,4S)-1-(2-Benzyloxy-ethyl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid tert-butyl ester → 1-(2-Hydroxy-ethyl)-2-oxa-3-aza-bicyclo[2.2.2]octane-3-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]2[CH2:14][CH2:15][C@:10]([CH2:16][CH2:17][O:18]CC3C=CC=CC=3)([CH:11]=[CH:12]2)[O:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:12][CH2:11][C:10]([CH2:16][CH2:17][OH:18])([CH2:15][CH2:14]2)[O:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
1 g Pd—C is placed into an round-bottom flask under an argon atmosphere and covered with ethanol. A solution of (1S,4S)-1-(2-benzyloxy-ethyl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid tert-butyl ester (10) (2 g, 5.8 mmol) in 58 ml of ethanol is added and the mixture is hydrogenated at rt for 6 h. Then the mixture is filtrated over celite and evaporated under reduced pressure. The product was used in the next step without further purification.