Formic Acid → Methyl 8-bromo-1-formyl-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate

HRID 1810798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1810798
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[Br:11][C:12]1[CH:13]=[CH:14][C:15]2[NH:22][CH2:21][CH2:20][CH2:19][C:18]([C:23]([O:25][CH3:26])=[O:24])=[CH:17][C:16]=2[CH:27]=1>C1COCC1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]2[N:22]([CH:1]=[O:2])[CH2:21][CH2:20][CH2:19][C:18]([C:23]([O:25][CH3:26])=[O:24])=[CH:17][C:16]=2[CH:27]=1

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 68650133Methyl 8-bromo-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate

Produkt 1

HCID 86595586Methyl 8-bromo-1-formyl-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

Formic acid (5.96 ml) was added to acetic anhydride (12.2 ml) at 0° C. and then the mixture was stirred under nitrogen atmosphere at 55° C. for 2 hours. After cooling to 0° C., THF (150 ml) was added, and further a solution of methyl 8-bromo-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate (8.5 g) in THF (100 ml) was added dropwise under nitrogen atmosphere. The mixture was returned to room temperature and stirred for 5 hours, after which the solvent was distilled off under reduced pressure. The reaction material was diluted with ethyl acetate, followed by washing with saturated sodium bicarbonate, water and saturated brine. The resultant was dried with magnesium sulfate, after which the solvent was distilled off under reduced pressure, and the resulting residue was washed with hexane to give methyl 8-bromo-1-formyl-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxylate (8.3 g) as colorless crystals.

Aufarbeitung

  1. temperatureAfter cooling to 0° C.
  2. customwas returned to room temperature
  3. stirringstirred for 5 hours
  4. distillationafter which the solvent was distilled off under reduced pressure
  5. additionThe reaction material was diluted with ethyl acetate
  6. washby washing with saturated sodium bicarbonate, water and saturated brine
  7. dry with materialThe resultant was dried with magnesium sulfate
  8. distillationafter which the solvent was distilled off under reduced pressure
  9. washthe resulting residue was washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-9f7a3e5fe8274a0faab7d215f15f891c
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362058B2

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