(Diethylamino)sulfur trifluoride → 1,4-dibenzyl-2-(R)-fluoromethylpiperazine

HRID 1864486Notes

Reaction equation

HRID 1864486 reaction equation
CCN(S(F)(F)[F:7])CC.[CH2:10]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][C@@H:18]1[CH2:30]O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH2:10]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][C@@H:18]1[CH2:30][F:7])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 9994741[(2R)-1,4-dibenzylpiperazin-2-yl]methanol

Product 1

HCID 574361011,4-dibenzyl-2-(R)-fluoromethylpiperazine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To an ice cooled solution of DAST (2 equivalents) in methylene chloride under N2 was added the alcohol prepared in Step 4 in methylene chloride dropwise. The yellow solution was stirred at 0° C. to room temperature for 20 hours. The reaction was diluted with NaHCO3, and the organic layer was separated and dried over sodium sulfate. The crude product was chromatographed on silica gel eluting with 10-50% EtOAc/hexanes giving the desired title compound as a yellow oil (40%).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. customThe crude product was chromatographed on silica gel eluting with 10-50% EtOAc/hexanes giving the desired title compound as a yellow oil (40%)

Sources & evidence

ORD record
ord-cae19968391b47d29afad4c8ae81a512
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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