Carbon Dioxide → HCID 69134515, Verbindung

HRID 917686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 917686
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][Si](C(C)(C)C)(C)C)[CH:6]=[CH:5]2.C([Li])CCC.C(=O)=O.[CH2:28]([O:35][CH:36]1[CH2:41][CH2:40][C:39](=[O:42])[CH:38]([CH2:43][N:44]([CH3:46])[CH3:45])[CH2:37]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1.CCCCCC.O>[CH2:28]([O:35][CH:36]1[CH2:41][CH2:40][C:39]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]3)([OH:42])[CH:38]([CH2:43][N:44]([CH3:46])[CH3:45])[CH2:37]1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

8

Edukt 4

HCID 280Carbon DioxideHCID 10999837HCID 10999837, VerbindungHCID 134730832-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthaleneHCID 178418339Butyllithium

Produkt 1

HCID 69134515HCID 69134515, VerbindungAusbeute 70,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

3.87 g (6-bromonaphthalen-2-yloxy)-tert.-butyldimethylsilane were dissolved in 19 ml THF p.a., 6.0 ml 1.6 M butyl lithium solution in hexane added dropwise with dry ice cooling, briefly stirred, then a solution of 2.00 g 4-benzyloxy-2-dimethylaminomethylcyclohexanone in 20 ml THF p.a. added dropwise and stirred for 1 hour while slowly heating. For working up, 4 ml water were added to the ice bath, the organic phase separated, the aqueous phase extracted twice with diethyl ether, the combined organic phases dried by sodium sulphate, filtered and concentrated. The crude product obtained (5.00 g) was chromatographed with ethyl acetate/methanol (V/V=1:1) on silica gel. 2.20 g 6-(4-benzyloxy-2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-naphthalen-2-ol were obtained and converted into the corresponding hydrochloride (1.33 g) in the same way as in AAV 1.

Aufarbeitung

  1. additionadded dropwise
  2. stirringstirred for 1 hour
  3. temperaturewhile slowly heating
  4. customthe organic phase separated
  5. extractionthe aqueous phase extracted twice with diethyl ether
  6. dry with materialthe combined organic phases dried by sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product obtained (5.00 g)
  10. customwas chromatographed with ethyl acetate/methanol (V/V=1:1) on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9a8e8e931b6d4e308bb77af68f3a02c1
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273952B2

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