Dimethylformamide → BOC-aminoether

HRID 1007574Notes

Reaction equation

HRID 1007574 reaction equation
[C:1](OC(N1CCC(O)CC1)=O)([CH3:4])([CH3:3])[CH3:2].[C:15](=[O:18])([O-:17])[O-:16].[Cs+].[Cs+].C[N:22](C=O)C>FC1C=CC(C(F)(F)F)=CC=1>[C:15]([O:17][NH2:22])([O:16][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 11992149BOC-aminoetherYield 81%

Reagents, catalysts & solvents 1

HCID 67873Benzene, 1-fluoro-4-(trifluoromethyl)-Catalyst

Procedure

Part A: A solution of N-(tert-butyloxycarbonyl)-4-piperidinol (5.00 g, 2.48 mmol), 4-fluorobenzo-trifluoride (3.46 mL, 2.73 mmol), and cesium carbonate (12.1 g, 3.72 mmol) in DMF (60 mL) was heated at 120 degrees Celsius under an atmosphere of nitrogen for 2 days. The mixture was concentrated, diluted with H2O, and extracted with ethyl acetate. The organic layer was washed with H2O and brine, dried with MgSO4, and concentrated in vacuo. Chromatography (on silica, ethyl acetate/hexane) provided the BOC-aminoether as a white solid (6.97 g, 81%); Anal. calculated. for C17H22NO3F3: C, 59.12; H, 6.42; N, 4.06. Found: C, 59.29; H, 6.47; N, 3.99.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with H2O
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with H2O and brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-564d61f4c66d43b5939e96b599eabb07
Source dataset
uspto-grants-2004_09
Patent number
US06794511B2

Reaction notes

Loading…