Methanol → HCID 56985609, compound

HRID 1584553Notes

Reaction equation

HRID 1584553 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11].[C:13](OC)(=[O:20])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].CO>CCCCCCC.CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[C:13]([O:10][CH:5]1[CH2:6][C:7]([CH3:8])([CH3:9])[N:2]([OH:1])[C:3]([CH3:12])([CH3:11])[CH2:4]1)(=[O:20])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 3

HCID 887MethanolHCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 7820Dimethyl Succinate

Product 1

HCID 56985609HCID 56985609, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8900HeptaneSolvent

Procedure

A solution of 6.0 g (35 mmol) of 1-oxyl-2,2,6,6-tetramethyl-4-hydroxypiperidine and 11.4 g (78 mmol) dimethyl succinate in 60 mL of heptane is brought to reflux. 0.05 mL of tetraisopropyl orthotitanate is added and the reaction mixture is refluxed for 16 hours while the evolved methanol is trapped in a Dean-Stark trap. The reaction mixture is then concentrated and the title compound is isolated as a red oil after column chromatography and melts at 76° C.

Workup

  1. temperatureto reflux
  2. concentrationThe reaction mixture is then concentrated

Sources & evidence

ORD record
ord-f5844f3b4ff94aa084c0e639f3a076e9
Source dataset
uspto-grants-1999_08
Patent number
US05932735

Reaction notes

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