Dichloromethane → HCID 58995014, compound

HRID 536978Notes

Reaction equation

HRID 536978 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:7][CH:6]([OH:8])[CH2:5][C:4]([CH3:10])([CH3:9])[N:3]1[CH2:11][C:12]([F:15])([F:14])[F:13].C(Cl)Cl>C([O-])(O)=O.[Na+]>[CH3:1][C:2]1([CH3:16])[CH2:7][C:6](=[O:8])[CH2:5][C:4]([CH3:9])([CH3:10])[N:3]1[CH2:11][C:12]([F:14])([F:15])[F:13]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 688303842,2,6,6-Tetramethyl-1-(2,2,2-trifluoro-ethyl)-piperidin-4-ol

Product 1

HCID 58995014HCID 58995014, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2,2,6,6-tetramethyl-1-(2,2,2-trifluoro-ethyl)-piperidin-4-ol (780 mg, 3.25 mmol; J. Phys. Org. Chem., 16(3), 175-182 (2003)) in DCM (50 mL) Dess-Martin periodinane (1.6 g, 3.2 mmol; Adv. Syn. Catalysis, 346, 111-124 (2004)) was added portionwise at 0° C. The resulting mixture was stirred at RT for 48 h, diluted with satd NaHCO3 (50 mL) and was extracted with DCM (3×25 mL). The organic layers were combined, dried (Na2SO4) and concentrated in vacuo. The resulting oil was chromatographed on silica (10-50% EtOAc/hexane) to obtain the title compound 309 mg, 40%. Mass spectrum (ESI, m/z): Calcd. for C11H18F3N, 238.1 (M+H). found 238.0.

Workup

  1. extractionwas extracted with DCM (3×25 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe resulting oil was chromatographed on silica (10-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-3a686fda18d2475496f358085b47f1f9
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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