Chlorotrimethylsilane → Methyl 4-(piperidin-4-yl)butanoate

HRID 1097288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097288
[CH3:1][Si](Cl)(C)C.[NH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:8][CH2:7]1>CO>[CH3:1][O:16][C:15](=[O:17])[CH2:14][CH2:13][CH2:12][CH:9]1[CH2:10][CH2:11][NH:6][CH2:7][CH2:8]1

Komponenten

4

Edukt 2

HCID 6397ChlorotrimethylsilaneHCID 51677024-(Piperidin-4-yl)butanoic acid

Produkt 1

HCID 21462751Methyl 4-(piperidin-4-yl)butanoateAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Trimethylsilyl chloride (9.2 ml, 72.46 mmol) was added to a solution of 4-piperidin-4-yl-butyric acid (1) (5.00 g, 24.15 mmol) dissolved in anhydrous methanol (100 mL). The resulting solution was stirred at room temperature for 48 hours, and concentrated under vacuum to complete dryness to give 2 (4.50 g, 97%) as a white solid, which was used directly in the next step without further purification: 1H NMR (300 MHz, CD3OD) δ 1.20-1.46 (m, 4H), 1.52-1.74 (m, 3H), 1.96 (d, 2H), 2.35 (t, 2H), 2.96 (t, 2H), 3.36 (t, 2H), 3.68 (s, 3H); ESI MS m/z 186 [C10H19NO2+H]+.

Aufarbeitung

  1. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5852ea171c3842fe9dcd0c6d841c6200
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143256B2

Notizen zur Reaktion

Wird geladen…