Sodium Hydroxide → HCID 67596932, compound

HRID 1600979Notes

Reaction equation

HRID 1600979 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([OH:15])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:16].[Na+].Cl[CH2:19][CH:20]([OH:29])[CH2:21][CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1>C(O)C>[C:12]([OH:13])(=[O:29])[C:7]([OH:6])=[O:16].[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[O:15][CH2:19][CH:20]([OH:29])[CH2:21][CH2:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21187957HCID 21187957, compoundHCID 22465338HCID 22465338, compound

Product 1

HCID 67596932HCID 67596932, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared according to the method described in Example 24b) from 3-cyclopentyloxy-4-methoxyphenol (0.835 g), ethanol (10 ml), aqueous sodium hydroxide (2 M, 2.5 ml) and (±)-α-(chloromethyl)-3-pyridinepropanol (0.760 g, Example 24a) to give the title compound as a yellow oil. This was purified by column chromatography over silica eluting with dichloromethane:ethanol and further purified by preparative normal-phase HPLC on a Dynamax™ Silica column with dichloromethane:ethanol (19:1). The purified material was then converted to the oxalate salt by treatment with excess oxalic acid in diethyl ether to give the title compound as a white solid (0.197 g).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-e663326027db4ed998fd54c44851a297
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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