Triethylamine → Tert-butyl-dimethyl-(3-piperidylmethoxy)silane

HRID 239961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 239961
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1.C(N(CC)CC)C.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl>[C:16]([Si:20]([CH3:23])([CH3:22])[O:8][CH2:7][CH:3]1[CH2:4][CH2:5][CH2:6][NH:1][CH2:2]1)([CH3:19])([CH3:18])[CH3:17]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 107308Piperidin-3-ylmethanol

Produkt 1

HCID 58992622Tert-butyl-dimethyl-(3-piperidylmethoxy)silaneAusbeute 60,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of piperidin-3-ylmethanol (2.10 g, 0.018 mol) in CH2Cl2 (20 mL) is added triethylamine (5.53 g, 0.0547 mol) followed by t-butyldimethylchlorosilane (4.127 g, 0.0275 mol) and the reaction mixture is stirred at room temperature. After 24 hours, the reaction mixture is washed with water, saturated solution of NaHCO3, and brine. The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (silica gel) over a gradient using 0-10% MeOH in dichloromethane to afford the title compound (2.50 g, 60%). Mass spectrum (m/z): 231.2 (M+1).

Aufarbeitung

  1. washthe reaction mixture is washed with water, saturated solution of NaHCO3, and brine
  2. dry with materialThe combined organic layers are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by flash chromatography (silica gel) over a gradient

Quellen und Nachweise

ORD-Eintrag
ord-22e62c1f9d7e42269b11779880b44f4d
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642768B2

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