(Diethylamino)sulfur trifluoride → HCID 178516222, compound

HRID 1672726Notes

Reaction equation

HRID 1672726 reaction equation
O[C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH2:4][CH2:3]1.CCN(S(F)(F)[F:20])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:20][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 178516223HCID 178516223, compound

Product 1

HCID 178516222HCID 178516222, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-1-(4-hydroxy-cyclohexyl)-pyrrolidin-2-one in CH2Cl2 at −30° C., add 786 mL of DAST dropwise. Allow the resulting mixture to warm up to room temp and let stand for 1 h. To the solution, add 10 mL of 5% aq NaHCO3 and allow to stand at room temp for 1 h. Extract the aqueous layer by CH2Cl2 twice (2×10 mL) and then dry the organic layer over Na2SO4, filter and concentrate. Purify the crude material by chromatography to yield the title compound: mass spectrum (m/z): 186 (M+1).

Workup

  1. waitto stand at room temp for 1 h
  2. extractionExtract the aqueous layer by CH2Cl2 twice (2×10 mL)
  3. dry with materialdry the organic layer over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the crude material by chromatography

Sources & evidence

ORD record
ord-57904fb9cf8547d3b51be8a130fd8b02
Source dataset
uspto-grants-2011_08
Patent number
US07998999B2

Reaction notes

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