(Diethylamino)sulfur trifluoride → HCID 68953227, compound

HRID 2384933Notes

Reaction equation

HRID 2384933 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:10]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11]2)O)=[CH:4][CH:3]=1.CCN(S(F)(F)[F:22])CC>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([F:22])[CH:10]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 68949993HCID 68949993, compound

Product 1

HCID 68953227HCID 68953227, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cool a solution of (4-bromo-phenyl)-(1-methyl-pyrrolidin-3-yl)-methanol in CH2Cl2 (6.5 mL) to 0° C. Add slowly a solution of DAST (0.1 mL, 0.78 mmol) in CH2Cl2. Stir the mixture at RT overnight. Cool the mixture to 0° C., then carefully quench with saturated NaHCO3 (exothermic and gas evolution). Extract the aqueous layer with CH2Cl2. Dry the combined organic phases with Na2SO4, filter, and concentrate. Purify the crude material by flash chromatography, collecting all the fractions as the product does not show by UV. Elute with 5-10% MeOH (2 N NH3)/CH2Cl2 to give 0.049 g (35%) of the title compound. LC-MS/ES m/z (79Br) 272.0 [M+H]+.

Workup

  1. temperatureCool the mixture to 0° C.
  2. customcarefully quench with saturated NaHCO3 (exothermic and gas evolution)
  3. extractionExtract the aqueous layer with CH2Cl2
  4. dry with materialDry the combined organic phases with Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude material by flash chromatography
  8. customcollecting all the fractions as the product
  9. washElute with 5-10% MeOH (2 N NH3)/CH2Cl2

Sources & evidence

ORD record
ord-0628ec7f7eb04761807942d3c90d0d6f
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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