4-Bromo-4-[bromo(4-methoxycarbonylphenyl)methyl]piperidine-1-carboxylic tert-butyl ester → HCID 10834544, Verbindung

HRID 353437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 353437
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](Br)([CH:14]([Br:25])[C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23]C)=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([Br:25])[C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 105291254-Bromo-4-[bromo(4-methoxycarbonylphenyl)methyl]piperidine-1-carboxylic tert-butyl ester

Produkt 1

HCID 10834544HCID 10834544, VerbindungAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of compound 4 (5.4 g 11 mmol) in methanol (300 mL) and 2.0 M NaOH (100 mL) was heated at 40° C. for 3 hrs. The solid was collected by filtration, and dried overnight under vacuum. The dry salt was dissolved in 40% acetonitrile/water, and was adjusted to pH 2 using concentrated HCl. The desired product compound 5 (3.8 g, 87%) was isolated as a white powder by filtration: 1H NMR (CDCl3) δ1.45 (s, 9H), 2.22 (dd, J=5.5 Hz, 6.1 Hz, 2H), 2.64 (dd, J=5.5 Hz, 6.1 Hz, 2H), 3.34 (dd, J=5.5 Hz, 6.1 Hz, 2H), 3.54 (dd, J=5.5 Hz, 6.1 Hz, 2H), 7.35 (d, J=6.7 Hz, 2H), 8.08 (d, J=6.7 Hz, 2H); 13 C NMR (CDCl3) δ28.3, 31.5, 34.2, 44.0, 115.3, 128.7, 129.4 130.3, 137.7, 145.2, 154.6, 170.3.

Aufarbeitung

  1. filtrationThe solid was collected by filtration
  2. customdried overnight under vacuum
  3. dissolutionThe dry salt was dissolved in 40% acetonitrile/water

Quellen und Nachweise

ORD-Eintrag
ord-4466e2680ab747aeb1d068c0b944a7ef
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06753335B2

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