(Diethylamino)sulfur trifluoride → 1-benzhydryl-3-fluoroazetidine

HRID 2201668Notes

Reaction equation

HRID 2201668 reaction equation
CCN(S(F)(F)[F:7])CC.[CH:10]([N:23]1[CH2:26][CH:25](O)[CH2:24]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[CH:10]([N:23]1[CH2:26][CH:25]([F:7])[CH2:24]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 73305071-benzhydryl-3-fluoroazetidineYield 30.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DAST (26.46 g, 0.164 mol) was added to a solution of Compound 19-2 (13.1 g, 0.0547 mol) in dry DCM (200 mL) at 0° C. The reaction mixture was stirred at room temperature overnight. The end of the reaction was monitored with TLC (petroleum ether/ethyl acetate=5:1). The reaction mixture was poured into ice water, extracted with DCM, washed with saturated brine, dried over anhydrous Na2SO4, and the organic layer was concentrated under reduced pressure, the resulting crude product was purified by column chromatography (petroleum ether/ethyl acetate=150:1) to give Compound 19-3 (4.0 g, 30% yield) as a white solid.

Workup

  1. extractionextracted with DCM
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customthe resulting crude product was purified by column chromatography (petroleum ether/ethyl acetate=150:1)

Sources & evidence

ORD record
ord-39f0b24062904d6dbb3215b0fd35dbcb
Source dataset
uspto-grants-2016_06
Patent number
US09365499B2

Reaction notes

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