Diethyl aminosulfur trifluoride → HCID 178515020, compound

HRID 271333Notes

Reaction equation

HRID 271333 reaction equation
O[CH:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH2:7][CH2:6]1.C(S(F)(F)([F:34])(CC)N)C>ClCCl>[F:34][CH:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 53748433Diethyl aminosulfur trifluorideHCID 178515021HCID 178515021, compound

Product 1

HCID 178515020HCID 178515020, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1 g of trans-2-[4-(2-hydroxy-2-phenyl-ethoxy)-cyclohexyl]-isoindole-1,3-dione in 100 mL of dichloromethane cooled to −78° C. under nitrogen atmosphere was added 1.2 g of diethyl-amino sulfur-trifluoride. The mixture was allowed to warm and stir for 24 h, then quenched with 25 mL of saturated sodium carbonate. After stirring for 15 min, the mixture was diluted with 25 mL of dichloromethane and the layers separated. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. Chromatography over silica gel eluting with a gradient of 2%-30% ethyl acetate in hexane gave 0.7 g of product as a white crystalline solid: 1H NMR (400 MHz, CDCl3) 7.8 (m, 2H), 7.7 (t, 1H), 7.4-7.3 (m, 5H), 5.6 (dd, 1H), 4.1 (m, 1H), 3.9-3.65 (complex m, 2H), 3.45 (m, 1H), 2.3 (dd, 2H), 2.2 (m, 2H), 1.8 (d, 2H), 1.4 (dd, 2H).

Workup

  1. temperatureto warm
  2. customquenched with 25 mL of saturated sodium carbonate
  3. stirringAfter stirring for 15 min
  4. additionthe mixture was diluted with 25 mL of dichloromethane
  5. customthe layers separated
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3992412f53004376a193ab7c91c814a0
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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