Aminoacetaldehyde dimethyl acetal → 3-Diphenylmethoxy-1-(2,2-dimethoxyethyl)-6-hydroxymethyl-4-pyridone

HRID 704653Notes

Reaction equation

HRID 704653 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[CH:7][CH:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14](OC)=[CH:13][CH:12]=2)[C:5](=[O:19])[CH:4]=1.[CH3:20][O:21][CH:22]([O:25][CH3:26])[CH2:23]N.C(Cl)(Cl)Cl.CO>CO>[C:11]1([CH:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[O:9][C:6]2[C:5](=[O:19])[CH:4]=[C:3]([CH2:2][OH:1])[N:8]([CH2:23][CH:22]([O:25][CH3:26])[O:21][CH3:20])[CH:7]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 200727056-Hydroxymethyl-3-(p-methoxybenzyl)oxy-4-pyridoneHCID 21584188Chloroform methanol

Product 1

HCID 150581923-Diphenylmethoxy-1-(2,2-dimethoxyethyl)-6-hydroxymethyl-4-pyridone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3.33 g of 6-hydroxymethyl-3-(p-methoxybenzyl)oxy-4-pyridone in 20 ml of methanol is added 11.35 g of 2,2-dimethoxyethylamine at room temperature, and the mixture is stirred for 3 days. The reaction mixture is condensed under reduced pressure, and subjected to flash column chromatography on 100 g of Wako-Gel C-300 (manufactured by Wako Pure Chemical Industries, Ltd.) with an eluent of chloroform-methanol (20:1) to perform separation and purification. The title compound is obtained as colorless foam in a yield of 2.062 g.

Workup

  1. customcondensed under reduced pressure
  2. customseparation and purification

Sources & evidence

ORD record
ord-d1777ba00c0b437e9f252ccf32e94f03
Source dataset
uspto-grants-1991_01
Patent number
US04988686

Reaction notes

Loading…