Water → cis-2-Triphenylmethylaminocyclohexanol

HRID 2399734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2399734
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[OH:9].[C:10]1([C:16](Cl)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.O>C(Cl)Cl>[C:10]1([C:16]([NH:2][C@H:3]2[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]2[OH:9])([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 12228413(1R,2S)-2-aminocyclohexan-1-ol hydrochloride

Produkt 1

HCID 54233547cis-2-Triphenylmethylaminocyclohexanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of cis-2-aminocyclohexanol hydrochloride (4.88 g; 32 mmol) (William S. Johnson and Elliot N. Schubert, J.A.C.S., Vol. 72, pp. 2187-2190 (1950), triphenylmethylchloride (10.7 g; 38.4 mmol) and triethylamine (16 ml; 115 mmol) in 250 ml methylene chloride are refluxed for 3 hrs. then stirred at room temperature overnight. The mixture is poured into H2O and extracted with CH2Cl2 (200 ml), dried (Na2SO4) concentrated in vacuo and flash chromatographed using 9:1 7:1; hexane:EtOAc to obtain cis-2-triphenylmethylaminocyclohexanol which is used directly in the next step.

Aufarbeitung

  1. extractionextracted with CH2Cl2 (200 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo and flash
  4. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-76b8b4c2cdec433c9a174a2e1b9b67bd
Quelldatensatz
uspto-grants-1995_09
Patentnummer
US05451596

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