(Diethylamino)sulfur trifluoride → 3-Fluoroproline

HRID 415874Notes

Reaction equation

HRID 415874 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

HCID 123472(Diethylamino)sulfur trifluorideHCID 186347293-Hydroxyproline methyl ester

Product 1

HCID 544367383-Fluoroproline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

  1. stirringIt was stirred at rt for 16 h
  2. washwashed with cold saturated sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. 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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