Acetic Acid → 220045-89-6

HRID 1109312

Reaktionsgleichung

Reaktionsgleichung von HRID 1109312
C(N)(C)(C)C.[C:6]([NH:10][CH2:11][CH:12]([OH:25])[CH2:13][O:14][C:15]1[C:24]2[CH2:23][CH:22]=CC[C:19]=2[CH:18]=[CH:17][CH:16]=1)([CH3:9])([CH3:8])[CH3:7].[C:26]([O:29]I)(=O)[CH3:27].C(O)(=[O:33])C>[Ag]I>[CH3:7][C:6]([NH:10][CH2:11][CH:12]([OH:25])[CH2:13][O:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[CH2:27][C@@H:26]([OH:29])[C@@H:22]([OH:33])[CH2:23][C:24]=12)([CH3:9])[CH3:8]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 6385Tert-ButylamineHCID 11087015HCID 11087015, VerbindungHCID 11446761HCID 11446761, Verbindung

Produkt 1

HCID 39147220045-89-6

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24563Silver iodideKatalysator

Versuchsvorschrift

Subsequently Hauck in Canadian Letters Patent 1,041,544 attempted to separate the four optical cis isomers of 2,3-cis-1,2,3,4-tetrahydro-S-[2-hydroxy-3-(tert-butylamino) propoxy]-2,3-naphthalenediol in order to determine the best of these isomers. The processes of manufacture (See pages 4, 5 and 6 of the Patent and example 4 at pages 18 and of the patent) employ water. Crystallization of isomer product is from chloroform. In Hauck's laboratory procedure resulting 1-(2,3-epoxypropoxy)-5,8-dihydronaphthalene is isolated and subsequently reacted with t-butylamine in a high pressure reactor. The resulting dl-1-(tert-butylamino)-3-(5,8-dihydronaphthyl)oxyl-2-propanol is then cis hydroxylated with wet acetic acid, silver iodide, and the resulting acetoxy iodide is hydrolysed with base and finally subjected to catalytic hydrogenation to afford crude Nadolol.

Aufarbeitung

  1. customis isolated

Quellen und Nachweise

ORD-Eintrag
ord-26ef28bfcba64683971d76ca8f18c42a
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05319141

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