Dimethylformamide → BOC-aminoether

HRID 2121447Notes

Reaction equation

HRID 2121447 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° C. under N2 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-3a987048a39445208ab700af7944adbf
Source dataset
uspto-grants-2004_02
Patent number
US06696449B2

Reaction notes

Loading…