(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 53419027, compound

HRID 245139

Reaction equation

HRID 245139 reaction equation
COCCN(S(F)(F)[F:11])CCOC.O[CH:15]1[CH2:20][CH2:19][N:18]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH2:17][CH2:16]1>>[F:11][CH:15]1[CH2:20][CH2:19][N:18]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 9835508tert-Butyl 4-hydroxy-[1,4'-bipiperidine]-1'-carboxylate

Product 1

HCID 53419027HCID 53419027, compoundYield 60%

Conditions

Temperature
-78 °C

Procedure

Deoxo-Fluor® was added to a solution of 1,1-dimethylethyl 4-hydroxy-1,4′-bipiperidine-1′-carboxylate (0.500 g, 1.76 mmol) dropwise at −78° C. The mixture was maintained at −78° C. for 30 min before it was warmed to room temperature and stirred for 2 h. The mixture was washed with saturated aqueous sodium bicarbonate. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified via column chromatography (1:200 methanol/methylene chloride) to afford 1,1-dimethylethyl 4-fluoro-1,4′-bipiperidine-1′-carboxylate (0.300 g, 60% yield) as a colorless oil.

Workup

  1. temperaturewas warmed to room temperature
  2. washThe mixture was washed with saturated aqueous sodium bicarbonate
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified via column chromatography (1:200 methanol/methylene chloride)

Sources & evidence

ORD record
ord-75d10dc72c0c4ec2945bb9e80a22e50c
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Linked notes

Loading…