(Diethylamino)sulfur trifluoride → HCID 89814611, compound

HRID 715114Notes

Reaction equation

HRID 715114 reaction equation
[CH2:1]([N:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][CH2:10][C:11]([CH3:14])(O)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(S(F)(F)[F:28])CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([N:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][CH2:10][C:11]([F:28])([CH3:14])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 79309201HCID 79309201, compound

Product 1

HCID 89814611HCID 89814611, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a −78° C. solution of 4-(dibenzylamino)-2-methylbutan-2-ol (110.0 g, 0.39 mol) in DCM (1 L) drop-wise with diethylaminosulfur trifluoride (75 g, 0.47 mol) under N2, allow it to warm to RT and stir overnight. Re-cool the mixture to −78° C., treat drop-wise with saturated NaHCO3 (300 mL), warm to RT, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate to dryness and purify via silica gel chromatography (0.1-0.2% EtOAc/pet ether) to afford the title compound (44.0 g, 40% yield). MS (m/z): 286.2 (M+1).

Workup

  1. additionRe-cool the mixture to −78° C., treat
  2. temperaturewarm to RT
  3. extractionextract with EtOAc (3×)
  4. washwash the combined organics with brine
  5. dry with materialdry over Na2SO4
  6. concentrationconcentrate to dryness
  7. custompurify via silica gel chromatography (0.1-0.2% EtOAc/pet ether)

Sources & evidence

ORD record
ord-37500f6ee620457daad53839da26fd9a
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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