(Diethylamino)sulfur trifluoride → HCID 86629214, compound

HRID 2384937Notes

Reaction equation

HRID 2384937 reaction equation
C(N(S(F)(F)[F:7])CC)C.[Br:10][C:11]1[CH:24]=[CH:23][C:14]([O:15][CH:16]2[CH2:20][N:19]([CH3:21])[CH2:18][CH:17]2O)=[C:13]([O:25][CH3:26])[CH:12]=1>ClCCl>[Br:10][C:11]1[CH:24]=[CH:23][C:14]([O:15][C@H:16]2[C@@H:17]([F:7])[CH2:18][N:19]([CH3:21])[CH2:20]2)=[C:13]([O:25][CH3:26])[CH:12]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 68950152HCID 68950152, compound

Product 1

HCID 86629214HCID 86629214, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add diethylaminosulfur trifluoride (0.173 mL, 1.31 mmol) to a solution of 4-(4-bromo-2-methoxy-phenoxy)-1-methyl-pyrrolidin-3-ol (0.329 g, 1.09 mmol) in dichloromethane (7 mL) at −78° C. Warm the mixture to room temperature and stir overnight. Evaporate the mixture and purify the resulting residue by silica gel chromatography, eluting with 0-70% ethyl acetate/hexane to give 130 mg (39%) of the title compound as a light brown oil. LC-MS/ES m/z (81Br) 306.0 [M+H]+.

Workup

  1. customEvaporate the mixture
  2. custompurify the resulting residue by silica gel chromatography
  3. washeluting with 0-70% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d032fcc8c2ee436b934d1cde46cf8f3e
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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