Trifluoromethanesulfonic anhydride → 455954-80-0

HRID 1744679Notes

Reaction equation

HRID 1744679 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O=[C:17]1[CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:20][N:19]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:18]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[CH2:18][N:19]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH2:20][CH2:21][C:22]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 158529891-tert-Butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylate

Product 1

HCID 22228415455954-80-0Yield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (12.4 mL, 73.7 mmol) was added over approximately 0.1 h, via syringe, to a stirred solution of the product of step B (27.1 g, 67.0 mmol) and N,N-diisopropylethylamine (14.0 mL, 80.4 mmol) in methylene chloride (250 mL) at −78° C. After allowing to warm to ambient temperature overnight, the reaction mixture was quenched with saturated aqueous sodium bicarbonate, poured into water and extracted three times with methylene chloride. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient elution; 0–20% ethyl acetate/hexanes as eluent) afforded the title compound as an amber colored oil (17.6 g).

Workup

  1. customthe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  2. additionpoured into water
  3. extractionextracted three times with methylene chloride
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash chromatography on silica gel (gradient elution; 0–20% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record
ord-39ec9578abbe4cd8b0bd37917c37e8f9
Source dataset
uspto-grants-2006_03
Patent number
US07015235B2

Reaction notes

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