(Diethylamino)sulfur trifluoride → 3-Fluoroproline
Reaction equation
C[O:2][C:3](=[O:10])[C@@H:4]1[CH:8](O)[CH2:7][CH2:6][NH:5]1.CCN(S(F)(F)[F:17])CC>C(Cl)Cl>[F:17][CH:8]1[CH2:7][CH2:6][NH:5][C@@H:4]1[C:3]([OH:2])=[O:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the 3-hydroxyproline methyl ester in DCM at −78° C., DAST (4 eq.) was added dropwise with stirring. The reaction was slowly warmed to rt. It was stirred at rt for 16 h, then diluted with more DCM and washed with cold saturated sodium bicarbonate, dried over sodium sulfate, filtered, concentrated and purified by column chromatography (SiO2, 20-30% ethyl acetate/hexanes) to provide the desired 3-fluoroproline intermediate.
Workup
- stirringIt was stirred at rt for 16 h
- washwashed with cold saturated sodium bicarbonate
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- custompurified by column chromatography (SiO2, 20-30% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-33190da509b3481a9b3ae7c841fce7d6
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088804B2
Reaction notes
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