Methyl Acrylate → HCID 68501444, compound

HRID 1176554Notes

Reaction equation

HRID 1176554 reaction equation
[Na].[OH:2][C:3]1[CH:4]=[C:5]([CH:44]=[CH:45][C:46]=1[CH3:47])[CH2:6][O:7][CH:8]1[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[CH:16][CH:15]=2)[CH2:12][CH2:11][N:10]([C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[CH2:9]1.[C:48]([O:52][CH3:53])(=[O:51])[CH:49]=[CH2:50]>C(O)C>[CH3:33][O:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][O:24][CH2:23][CH2:22][CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH:13]2[CH2:12][CH2:11][N:10]([C:34]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])[CH2:9][CH:8]2[O:7][CH2:6][C:5]2[CH:44]=[CH:45][C:46]([CH3:47])=[C:3]([O:2][CH2:50][CH2:49][C:48]([O:52][CH3:53])=[O:51])[CH:4]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 5360545SodiumHCID 68500716HCID 68500716, compound

Product 1

HCID 68501444HCID 68501444, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The solution of 5.1 mg of sodium in 0.5 ml of ethanol is admixed with 0.626 g of benzyl 3-(3-hydroxy-4-methylbenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate and 15 ml of methyl acrylate and stirred at room temperature over 18 hours. The reaction mixture is concentrated by evaporation, and the residue is admixed with 25 ml of 0.5M HCl (cold) and extracted with tert-butyl methyl ether (2×25 ml). The organic phases are washed with brine (25 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.42 (1:1 EtOAc-heptane); Rt=6.00.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. extractionextracted with tert-butyl methyl ether (2×25 ml)
  3. washThe organic phases are washed with brine (25 ml)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1079491a79e744449fdb5547129b0927
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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