Trimethylsilyldiazomethane → 1-tert-Butyl 3-methyl piperidine-1,3-dicarboxylate

HRID 1723841Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1723841
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][Si](C=[N+]=[N-])(C)C>CO.C1(C)C=CC=CC=1>[CH3:17][O:15][C:14]([CH:10]1[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]1)=[O:16]

Komponenten

4

Edukt 2

HCID 167693TrimethylsilyldiazomethaneHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acid

Produkt 1

HCID 235906521-tert-Butyl 3-methyl piperidine-1,3-dicarboxylateAusbeute 83,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21867641Toluene methanolLösungsmittel

Versuchsvorschrift

To a room temperature solution of piperidine-1,3-dicarboxylic acid-1-tert-butyl ester (5.00 g, 21.81 mmol) in 20% MeOH/toluene (100 ml) was added 14.18 ml of (trimethylsilyl)diazomethane (2.0 M, 28.35 mmol) dropwise and the reaction was monitored by TLC until completion and then concentrated under reduced pressure to yield 4.44 g (83.7%) of piperidine-1,3-dicarboxylic acid 1-tert-butyl ester-3-methyl ester (Intermediate 53). 1H NMR (400 MHz, CDCl3) δ ppm 1.4 (s, 9H), 1.6 (d, J=3.4 Hz, 1H), 1.6 (m, 1H), 1.7 (m, 1H), 2.0 (m, 1H), 2.4 (m, 1H), 2.8 (m, 1H), 3.0 (s, 1 H), 3.7 (s, 3H), 3.9 (d, J=13.2 Hz, 1H), 4.1 (s, 1H).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-370f795a58284cb2b915c4aff436f940
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485636B2

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