Diisopropylethylamine → HCID 178485970, Verbindung

HRID 2057220Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2057220
[CH3:1][NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1.[CH:10]1[C:15]([O:16][C:17](Cl)=[O:18])=[CH:14][CH:13]=[C:12]([Cl:20])[CH:11]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:20][C:12]1[CH:13]=[CH:14][C:15]([O:16][C:17](=[O:18])[N:2]([C@H:3]2[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]2)[CH3:1])=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 178484843HCID 178484843, Verbindung

Produkt 1

HCID 178485970HCID 178485970, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 16.1 g (124.7 mmol) trans-4-methylamino-cyclohexanol in 40 ml CH2Cl2, 18.3 ml (130.9 mmol, 1.05 eq) 4-chlorophenylchloroformate and 22.4 ml (130.9 mmol, 1.05 eq) Huenigs base were added at 0° C. The solution was stirred at RT over night, diluted, and washed with 1M HCl, sat. aqueous NaHCO3 solution. The organic phase was dried over MgSO4. Column chromatography on silica gel with EtOAc:hexane 1:1 yielded 32.2 g (91%) trans-(4-Hydroxy-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester as white solid, MS: 283 (M, 1Cl).

Aufarbeitung

  1. additiondiluted
  2. washwashed with 1M HCl, sat. aqueous NaHCO3 solution
  3. dry with materialThe organic phase was dried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-f66c9d9bbd524c02a8df5b9f00ad8dc0
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335687B2

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