Ethanol → 4-[Bromo-(4-ethoxycarbonylamino-phenyl)-methyl]-piperidine-1-carboxylic Acid Tert-Butyl Ester

HRID 2120903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2120903
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([Br:24])[C:15]2[CH:20]=[CH:19][C:18](C(O)=O)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.C([N:44]([CH2:47]C)CC)C.[CH2:49]([OH:51])[CH3:50]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH:14]([Br:24])[C:15]2[CH:20]=[CH:19][C:18]([NH:44][C:47]([O:51][CH2:49][CH3:50])=[O:32])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 8471Triethylamine2×HCID 199401P,P-Diphenylphosphinic azideHCID 10834544HCID 10834544, Verbindung

Produkt 1

HCID 692435694-[Bromo-(4-ethoxycarbonylamino-phenyl)-methyl]-piperidine-1-carboxylic Acid Tert-Butyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a mixture of compound 51, prepared according to Scheme 6, (0.25 g, 0.625 mmole) in toluene (5 mL), was added diphenylphosphorylazide (0.192 g, 0.70 mmole) and triethylamine (0.1 mL, 0.7 mmole). After stirring the mixture under argon at 95° C. for two hours an excess of anhydrous ethanol (2 mL) and triethylamine (0.1 mL) were added and the solution was stirred at 95° C. for an additional 5 hours. After cooling to room temperature the reaction mixture was partitioned between water and diethyl ether. The ether was washed with water, dried over magnesium sulfate and removed in vacuo to give the product (compound 88) as a tan foam (300 mg, 99% yield).

Aufarbeitung

  1. customprepared
  2. additionwere added
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. customwas partitioned between water and diethyl ether
  5. washThe ether was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customremoved in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-67cf9ed921eb4c6794379c5365d0bbb5
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693117B2

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