Potassium Iodide → tert-butyl 7-(benzyloxy)-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylate

HRID 645780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 645780
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CC(=O)CC>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([O:19][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 18173274tert-butyl 7-hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepine-3-carboxylate

Produkt 1

HCID 57437616tert-butyl 7-(benzyloxy)-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

7-Hydroxy-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester (PCT Int. Appl. (2002), WO 02/40471) (790 mg, 3 mmol), potassium carbonate (1.24 g, 9 mmol) and catalytic potassium iodide were suspended in 2-butanone (20 ml). Benzyl bromide (536 μL, 4.5 mmol) was added and the mixture heated at reflux for 24 hours. The solids were filtered and then washed with acetone. The filtrate was concentrated in vacuo and the crude oil purified by column chromatography, eluting with a mixture of ethyl acetate and hexane (1:4) to afford the title compound (D1) (1.06 g, 100%), 1H NMR (CDCl3) 7.44 (5H, m), 7.03 (1H, d, J 8.1 Hz), 6.77 (1H, s), 6.74 (1H, dd, J 8.1 & 2.4 Hz), 3.49 (4H, m), 2.84 (4H, m), 1.48 (9H, s).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux for 24 hours
  3. filtrationThe solids were filtered
  4. washwashed with acetone
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe crude oil purified by column chromatography
  7. washeluting with a mixture of ethyl acetate and hexane (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-878b2964d18a42f8a1db701c5973fb52
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07704994B2

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