(Diethylamino)sulfur trifluoride → HCID 89814257, compound

HRID 715120Notes

Reaction equation

HRID 715120 reaction equation
C(N(S(F)(F)[F:7])CC)C.[CH2:10]([N:17]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:18][CH2:19][CH2:20][C:21]([CH3:24])(O)[CH3:22])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[CH2:10]([N:17]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:18][CH2:19][CH2:20][C:21]([F:7])([CH3:24])[CH3:22])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 86222790HCID 86222790, compound

Product 1

HCID 89814257HCID 89814257, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add diethylaminosulfur trifluoride (17.9 g, 111 mmol) drop-wise to a −78° C. solution of 5-(dibenzylamino)-2-methylpentan-2-ol (11 g, 37 mmol) in DCM (100 mL), under N2, warm to RT and stir overnight. Pour the mixture into ice-water, neutralize with satd. NaHCO3, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate and purify via silica gel chromatography to afford the title compound (4.5 g, 41%). 1H NMR (400 MHz, DMSO-d6): δ 7.30-7.13 (m, 10H), 3.48 (s, 4H), 2.35 (m, 2H), 1.51-1.48 (m, 4H), 1.22 (d, J=21.2 Hz, 6H).

Workup

  1. extractionNaHCO3, extract with EtOAc (3×)
  2. washwash the combined organics with brine
  3. dry with materialdry over Na2SO4
  4. concentrationconcentrate
  5. custompurify via silica gel chromatography

Sources & evidence

ORD record
ord-961175d021224fc2b6c28d6d28e232bb
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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