Sodium Iodide → tert-Butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[3-(3-methoxypropyl)-2-oxo-2,3-dihydrobenzoxazol-5-ylmethoxy]piperidine-1-carboxylate

HRID 1176211Notes

Reaction equation

HRID 1176211 reaction equation
[CH3:1][O:2][C:3]1[CH:45]=[CH:44][CH:43]=[CH:42][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][C@@H:18]2[O:30][CH2:31][C:32]2[CH:33]=[CH:34][C:35]3[O:39][C:38](=[O:40])[NH:37][C:36]=3[CH:41]=2)=[CH:13][CH:12]=1.[H-].[Na+].Cl[CH2:49][CH2:50][CH2:51][O:52][CH3:53].[I-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:45]=[CH:44][CH:43]=[CH:42][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]2[O:30][CH2:31][C:32]2[CH:33]=[CH:34][C:35]3[O:39][C:38](=[O:40])[N:37]([CH2:49][CH2:50][CH2:51][O:52][CH3:53])[C:36]=3[CH:41]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 1189271-Chloro-3-methoxypropaneHCID 68503992HCID 68503992, compound

Product 1

HCID 68503770tert-Butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[3-(3-methoxypropyl)-2-oxo-2,3-dihydrobenzoxazol-5-ylmethoxy]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The solution of 0.206 g of tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-(3R,4R)-3-(2-oxo-2,3-dihydrobenzoxazol-5-ylmethoxy)piperidine-1-carboxylate in 2 ml of N,N-dimethylformamide is cooled to 0° C. with stirring and admixed with 12 mg of sodium hydride dispersion (60%). The mixture is stirred at 0° C. for 30 minutes and subsequently admixed with 0.048 ml of 1-chloro-3-methoxypropane and 5 mg of sodium iodide. The reaction mixture is stirred at 80° C. for 14 hours, cooled and poured onto water (40 ml). The mixture is extracted with ethyl acetate (2×40 ml). The organic phases are washed successively with water (2×40 ml) and brine (1×40 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue as a slightly yellowish oil by means of flash chromatography (SiO2 60F). Rf=0.25 (2:1 toluene-EtOAc); Rt=6.03.

Workup

  1. stirringThe mixture is stirred at 0° C. for 30 minutes
  2. stirringThe reaction mixture is stirred at 80° C. for 14 hours
  3. temperaturecooled
  4. additionpoured onto water (40 ml)
  5. extractionThe mixture is extracted with ethyl acetate (2×40 ml)
  6. washThe organic phases are washed successively with water (2×40 ml) and brine (1×40 ml)
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b9eab88a22d342e8877fb779e6eb3f2b
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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