Lithium Hexamethyldisilazide → HCID 67271943, Verbindung

HRID 597841

Reaktionsgleichung

Reaktionsgleichung von HRID 597841
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2].Cl[CH2:20][O:21][CH2:22][CH2:23][Cl:24].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Cl:24][CH2:23][CH2:22][O:21][CH2:20][C:3]1([C:1]#[N:2])[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:5][CH2:4]1

Komponenten

5

Edukt 3

HCID 2733832Lithium HexamethyldisilazideHCID 102908101-chloro-2-(chloromethoxy)ethaneHCID 22028286Benzyl 4-cyanopiperidine-1-carboxylate

Produkt 1

HCID 67271943HCID 67271943, VerbindungAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of benzyl 4-cyanopiperidine-1-carboxylate (10.0 g, 41 mmol) and 2-chloroethyl chloromethyl ether (6.3 mL, 49.2 mmol) in THF (80 mL) was cooled to −78° C. To this solution was added drop wise LiHMDS (50 mL, 50 mmol, 1N in THF) and the resulting mixture was gradually warmed to room temp over 5 h. The reaction was quenched with water and the organic phase was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (1:1 EtOAc/hexane) to give the title compound as yellow oil (11.9 g, 86% yield). 1H NMR (300 MHz, CDCl3) δ: 7.33-7.31 (5H, m), 5.10 (2H, d, J=5.9 Hz), 4.21 (2H, bs), 3.79-3.76 (2H, m), 3.63-3.60 (2H, m), 3.52-3.51 (2H, m), 3.09 (2H, bs), 1.96-1.92 (2H, m), 1.55-1.51 (2H, m).

Aufarbeitung

  1. customThe reaction was quenched with water
  2. washthe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (1:1 EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-9af7343dc09e4601873c16461fc5d8db
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897593B2

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