HCID 1222549, compound → HCID 54034265, compound

HRID 1463536Notes

Reaction equation

HRID 1463536 reaction equation
[C:1]([O:23][CH:24]1[CH2:29][C:28]([CH3:31])([CH3:30])[N:27]([OH:32])[C:26]([CH3:34])([CH3:33])[CH2:25]1)(=[O:22])[C:2]1[C:3](=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:4]([O:6][CH:7]1[CH2:12][C:11]([CH3:14])([CH3:13])[N:10]([OH:15])[C:9]([CH3:17])([CH3:16])[CH2:8]1)=[O:5]>[Pd].C(OC(=O)C)(=O)C>[C:4]([O:6][CH:7]1[CH2:12][C:11]([CH3:13])([CH3:14])[N:10]([O:15][C:7](=[O:6])[CH3:8])[C:9]([CH3:17])([CH3:16])[CH2:8]1)(=[O:5])[C:3]1[C:2](=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:1]([O:23][CH:24]1[CH2:29][C:28]([CH3:31])([CH3:30])[N:27]([O:32][C:4](=[O:5])[CH3:3])[C:26]([CH3:34])([CH3:33])[CH2:25]1)=[O:22]

Participants

4

Reactant 1

HCID 1222549HCID 1222549, compound

Product 1

HCID 54034265HCID 54034265, compoundYield 126.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 20.0 g (42 mmol) of di-(1-oxyl-2,2,6,6-tetramethyl-piperidin-4-yl) phthalate, 100 ml of acetic anhydride, and 500 mg of 5% Pd on C is hydrogenated in a Paar apparatus (50 psi, ambient temperature, 1 hour). Catalyst is filtered and solvent is evaporated. The residue is dissolved in 150 ml of ethyl acetate. The ethyl acetate solution is washed with 5% aqueous ammonia (2×100 ml), water (100 ml), and saturated sodium chloride (100 ml), then dried over magnesium sulfate and concentrated to obtain a crude solid. The crude product is recrystallized from methanol to obtain 14.9 g (64% yield) of a white crystalline solid, m.p. 172-175° C.

Workup

  1. customis hydrogenated in a Paar apparatus (50 psi, ambient temperature, 1 hour)
  2. filtrationCatalyst is filtered
  3. customsolvent is evaporated
  4. dissolutionThe residue is dissolved in 150 ml of ethyl acetate
  5. washThe ethyl acetate solution is washed with 5% aqueous ammonia (2×100 ml), water (100 ml), and saturated sodium chloride (100 ml)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto obtain a crude solid
  9. customThe crude product is recrystallized from methanol

Sources & evidence

ORD record
ord-d9e623858e73415c8b4d64b7f9314013
Source dataset
uspto-grants-1994_04
Patent number
US05300647

Reaction notes

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