Methanol → N-(1-acetyl-2,2,6,6-tetramethyl-4-piperidinyl)glycine(1-acetyl-2,2,6,6-tetramethyl-4-piperidinyl)ester

HRID 652207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 652207
[CH3:1][O:2][C:3](=[O:19])[CH2:4][NH:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([C:14](=[O:16])[CH3:15])[C:8]([CH3:18])([CH3:17])[CH2:7]1.[C:20]([N:23]1[C:28]([CH3:30])([CH3:29])[CH2:27]C(O)[CH2:25][C:24]1([CH3:33])[CH3:32])(=[O:22])[CH3:21].[NH2-].[Li+].CO>CCCCCCC.O>[C:20]([N:23]1[C:24]([CH3:33])([CH3:32])[CH2:25][CH:1]([O:2][C:3](=[O:19])[CH2:4][NH:5][CH:6]2[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([C:14](=[O:16])[CH3:15])[C:8]([CH3:18])([CH3:17])[CH2:7]2)[CH2:27][C:28]1([CH3:30])[CH3:29])(=[O:22])[CH3:21]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 24532Lithium amideHCID 145493121-(4-Hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)ethan-1-oneHCID 20199419N-(1-acetyl-2,2,6,6-tetramethyl-4-piperidinyl)glycine methyl ester

Produkt 1

HCID 13907927N-(1-acetyl-2,2,6,6-tetramethyl-4-piperidinyl)glycine(1-acetyl-2,2,6,6-tetramethyl-4-piperidinyl)esterAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8900HeptaneLösungsmittel2×

Versuchsvorschrift

To a four-necked flask equipped with a thermometer, a stirrer and a Deanstark trap were added 27 g (0.1 mole) of N-(1-acetyl-2,2,6,6-tetramethyl-4-piperidinyl)glycine methyl ester, 21.9 g (0.11 mole) of 1-acetyl-2,2,6,6-tetramethyl-4-piperidinol, 0.23 g of lithium amide and 100 g of heptane. The temperature was raised with stirring, and reaction was carried out at 98° to 105° C. for 6 hours, during which methanol was removed from the reaction system by means of the Deanstark trap. After completion of the reaction, the reaction solution was cooled, and water was added thereto to dissolve the product in the heptane layer. The heptane layer was separated and concentrated by removing heptane by distillation. The residue was purified by column chromatographic separation to obtain 32 g of N-(1-acetyl-2,2,6,6-tetramethyl-4-piperidinyl)glycine(1-acetyl-2,2,6,6-tetramethyl-4-piperidinyl)ester as a pale yellow liquid. Yield, 73% based on N-(1-acetyl-2,2,6,6-tetramethyl-4-piperidinyl)-glycine methyl ester.

Aufarbeitung

  1. customTo a four-necked flask equipped with a thermometer, a stirrer
  2. temperatureThe temperature was raised
  3. customreaction
  4. customwas removed from the reaction system by means of the Deanstark trap
  5. customAfter completion of the reaction
  6. temperaturethe reaction solution was cooled
  7. customThe heptane layer was separated
  8. concentrationconcentrated
  9. customby removing heptane
  10. distillationby distillation
  11. customThe residue was purified by column chromatographic separation

Quellen und Nachweise

ORD-Eintrag
ord-9d5162eb4def4d3f8226189749e3f025
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04670488

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