Tetrahydrofuran → tert-butyl N-[2-(4-fluorophenyl)-2-hydroxyethyl]-N-methylcarbamate

HRID 1351265Notes

Reaction equation

HRID 1351265 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[CH2:9][NH:10][CH3:11])=[CH:4][CH:3]=1.[C:13]([O:17][C:18](=[O:20])O)([CH3:16])([CH3:15])[CH3:14].O1CCCC1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[C:13]([O:17][C:18](=[O:20])[N:10]([CH2:9][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[OH:12])[CH3:11])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 3015642Mono-tert-butyl carbonateHCID 219434071-(4-Fluorophenyl)-2-(methylamino)ethan-1-ol

Product 1

HCID 69414015tert-butyl N-[2-(4-fluorophenyl)-2-hydroxyethyl]-N-methylcarbamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(4-fluorophenyl)-2-methylamino ethanol (the compound of Preparation Example 17) (9.7 g) and t-butylbicarbonate (10.0 g) in a mixed solvent of tetrahydrofuran solution (100 mL) and an aqueous solution of saturated sodium bicarbonate (50 mL) was stirred at room temperature for 1.5 hours. The solution was diluted with ethyl acetate, and washed with water and saturated sodium chloride water. After drying the organic layer with anhydrous sodium sulfate, the residue that was obtained by evaporating the solvent at reduced pressure was purified by silica gel column chromatography (hexane/ethyl acetate), and the title compound (9.5 g) was obtained as a colorless solid.

Workup

  1. washwashed with water and saturated sodium chloride water
  2. dry with materialAfter drying the organic layer with anhydrous sodium sulfate
  3. customthe residue that was obtained
  4. customby evaporating the solvent at reduced pressure
  5. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dbbe7d011d1a482e8a467cfb9c6dca6e
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

Loading…