Triethylamine → HCID 86700549, Verbindung

HRID 2176462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2176462
[Si:1]([O:18][CH2:19][C@@H:20]1[CH2:25][CH2:24][CH2:23][CH:22]([OH:26])[N:21]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:34](N(CC)CC)C>CO.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Si:1]([O:18][CH2:19][C@@H:20]1[CH2:25][CH2:24][CH2:23][CH:22]([O:26][CH3:34])[N:21]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 2

HCID 8471TriethylamineHCID 86700550HCID 86700550, Verbindung

Produkt 1

HCID 86700549HCID 86700549, VerbindungAusbeute 841,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)KatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To an ice cold solution of (2S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-6-hydroxypiperidine-1-carboxylate (2 g, 4.3 mmol) in methanol (20 mL) was added pyridinium p-toluenesulfonate (108 mg, 0.43 mmol). The reaction mixture was warmed to RT and stirred overnight. Triethylamine (87 mg, 0.86 mmol) was added, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (eluting with 0-15% EtOAc in petroleum ether), and combined with the product of three similar runs to provide the title intermediate (3.5 g).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (eluting with 0-15% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-8f9b9730059c4b49828dce69479cd223
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09066944B2

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