Methanol → 8-[2-Hydroxy-3-(2-methoxyphenoxy)propyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one

HRID 1389474Notes

Reaction equation

HRID 1389474 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][NH:3][C:2]1=[O:11].O1CC1C[C:15]1[C:16]([O:34][CH3:35])=[C:17]([O:21][C:22]2C=CC=[C:24](CC3OC3)[C:23]=2[O:32]C)[CH:18]=[CH:19][CH:20]=1.CO>C1(C)C=CC=CC=1>[CH3:35][O:34][C:16]1[CH:15]=[CH:20][CH:19]=[CH:18][C:17]=1[O:21][CH2:22][CH:23]([OH:32])[CH2:24][N:8]1[CH2:7][CH2:6][C:5]2([O:1][C:2](=[O:11])[NH:3][CH2:4]2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 887MethanolHCID 129541141-Oxa-3,8-diazaspiro(4.5)decan 2-oneHCID 86737432HCID 86737432, compound

Product 1

HCID 130166488-[2-Hydroxy-3-(2-methoxyphenoxy)propyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-oneYield 86.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3.12 g 1-oxa-3,8-diazaspiro[4.5]decan-2-one, 5.4 g 2,3-epoxypropyl-o-methoxyphenyl ether, 5 ml methanol and 10 ml toluene is heated at reflux for 24 hours. The solvent is evaporated and the residue filtered through 20 g silica gel with 10% methanol/methylene chloride. Evaporation of solvent and crystallization from diethyl ether affords 4.6 g 8-[3-(2-methoxyphenoxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one, mp 124°-125°.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 24 hours
  3. customThe solvent is evaporated
  4. filtrationthe residue filtered through 20 g silica gel with 10% methanol/methylene chloride
  5. customEvaporation of solvent and crystallization from diethyl ether

Sources & evidence

ORD record
ord-8c91b2a9954d4061a87269440b0d7ca5
Source dataset
uspto-grants-1981_01
Patent number
US04244961

Reaction notes

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