Water → HCID 86610005, compound

HRID 1176402Notes

Reaction equation

HRID 1176402 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])=[CH:13][CH:12]=2)[CH2:9][CH2:8][N:7]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:6]1.[H-].[Na+].[Cl:40][C:41]1[C:46]([CH2:47][C:48]([O:50][CH3:51])=[O:49])=[C:45](Cl)[N:44]=[C:43]([CH3:53])[N:42]=1.O>COCCOC>[Cl:40][C:41]1[N:42]=[C:43]([CH3:53])[N:44]=[C:45]([O:1][CH2:2][CH2:3][O:4][CH:5]2[CH:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[CH:15][CH:16]=3)[CH2:9][CH2:8][N:7]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:6]2)[C:46]=1[CH2:47][C:48]([O:50][CH3:51])=[O:49]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 19071353HCID 19071353, compoundHCID 68499161HCID 68499161, compound

Product 1

HCID 86610005HCID 86610005, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 1.95 g of tert-butyl 3-(2-hydroxyethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]-phenyl}piperidine-1-carboxylate (Example 14c) in 20 ml of 1,2-dimethoxyethane is admixed in portions at 0° C. with 0.195 g of sodium hydride dispersion (60%) and stirred for 30 minutes. A solution of 0.91 g of methyl (4,6-dichloro-2-methylpyrimidin-5-yl)acetate in 5 ml of dimethoxyethane is added dropwise and the reaction mixture is stirred at room temperature over 2.5 hours. The reaction mixture is admixed with water and extracted with tert-butyl methyl ether (3×). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.42 (1:1 EtOAc-heptane); Rt=6.10.

Workup

  1. stirringthe reaction mixture is stirred at room temperature over 2.5 hours
  2. extractionextracted with tert-butyl methyl ether (3×)
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-90c9378c7fe04de28e0043f070b27887
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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