(R)-1-[3-(t-butyl-dimethyl-silanyloxy)-phenyl-sulfanylcarbonyl]-pyrrolidine-2-carboxylic acid ethyl ester → (R)-1-(3-Hydroxy-phenylsulfanylcarbonyl)-pyrrolidine-2-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][Si](C(C)(C)C)(C)C)[CH:15]=1)=[O:12])=[O:5])[CH3:2]>C1COCC1>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=1)=[O:12])=[O:5])[CH3:2]Participants
3
Procedure
To the title B compound, (R)-1-[3-(t-butyl-dimethyl-silanyloxy)-phenylsulfanyl-carbonyl]-pyrrolidine-2-carboxylic acid ethyl ester (1.5 g, 3.66 mmol) in a flask at RT, is added 1 M solution of n-tetrabutylammonium fluoride (14.6 mL, 14.6 mmol) in THF and the reaction is stirred for 4 h. The reaction mixture is concentrated at reduced pressure, diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated. The crude (R)-1-(3-hydroxy-phenylsulfanylcarbonyl)-pyrrolidine-2-carboxylic acid ethyl ester is used in the next step without further purification.