Trityl chloride → N-trityl-1-hydroxytricyclo[3.3.1.13,7]decan-2-amine

HRID 1608575

Reaktionsgleichung

Reaktionsgleichung von HRID 1608575
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH:3]1[NH2:12])[CH2:9]2.[C:13]1([C:19](Cl)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[C:19]([NH:12][CH:3]1[CH:4]2[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9][C:2]1([OH:1])[CH2:11]3)[CH2:10]2)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

4

Edukt 2

HCID 6456Trityl chloride2×HCID 124667122-Aminoadamantan-1-ol

Produkt 1

HCID 54340516N-trityl-1-hydroxytricyclo[3.3.1.13,7]decan-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 1-hydroxytricyclo[3.3.1.13,7 ]decan-2-amine (0.47 g; 0.0028 mole), [prepared via a procedure of W. V. Curran and R. B. Angler, J. of Org. Chem., 94(11 ), 3668-70 (1969)] in dichloromethane (45 ml) is added triphenylmethyl chloride (0.78 g; 0.0028 mole) in dichloromethane (5 ml). This mixture is refluxed for 7 hours and then more triphenylmethyl chloride (0.35 g) is added and the reaction refluxed overnight. The reaction is stripped to dryness and the products separated via flash chromatography (eluted with 25% ethyl acetate/hexane) to obtain N-trityl-1-hydroxytricyclo[3.3.1.13,7 ]decan-2-amine which is used directly in step B.

Aufarbeitung

  1. temperatureThis mixture is refluxed for 7 hours
  2. temperaturethe reaction refluxed overnight
  3. customthe products separated via flash chromatography (eluted with 25% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-956548f962c1482eae9663a3053a9477
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05395846

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