Tetrabutylammonium Fluoride → (2S,5S)-2-Ethoxy-5-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH2:12][O:11][C@H:10]([O:23][CH2:24][CH3:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][OH:15])[CH2:12][O:11][C@H:10]([O:23][CH2:24][CH3:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
4
Procedure
Dissolve (2S,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2-ethoxymorpholine-4-carboxylic acid tert-butyl ester (0.39 g, 1.04 mmole) in tetrahydrofuran (3 mL) and add tetrabutylammonium fluoride (2.1 mL, 2.1 mmol, 1.0 M in tetrahydrofuran). Stir 45 minutes at room temperature, concentrate and purify (silica gel chromatography, eluting with 10:90 to 40:60 ethyl acetate:hexanes) to give the desired compound (252 mg, 92%).