(Diethylamino)sulfur trifluoride → HCID 66961388, compound

HRID 2247487Notes

Reaction equation

HRID 2247487 reaction equation
O[CH2:2][C@H:3]([N:11]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CCN(S(F)(F)[F:28])CC.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:28][CH2:2][C@H:3]([N:11]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluoride2×HCID 516892Sodium BicarbonateHCID 11065868(R)-2-(1-hydroxymethyl-2-phenylethyl)isoindole-1,3-dione

Product 1

HCID 66961388HCID 66961388, compoundYield 4.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-2-(1-hydroxymethyl-2-phenylethyl)isoindole-1,3-dione (1.20 g) was added to a methylene chloride (20 mL) solution of DAST (825 mg) at −78° C. and the reaction solution was agitated at room temperature. DAST (500 mg) was added to the reaction solution after 2 hours, and the reaction solution was agitated at 50° C. for 3 hours. Saturated sodium bicarbonate solution was added for reaction solution to the reaction solution after allowing the reaction solution to be cooled to room temperature, and the organic layer was partitioned. The organic layer was concentrated under reduced pressure after dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system), and 52 mg of the title compound was obtained.

Workup

  1. stirringthe reaction solution was agitated at 50° C. for 3 hours
  2. temperatureto be cooled to room temperature
  3. customthe organic layer was partitioned
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. dry with materialafter dried over anhydrous magnesium sulfate
  6. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-4c44c67fd706405eab28fda89dbce345
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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