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

HRID 30405

Reaktionsgleichung

Reaktionsgleichung von HRID 30405
[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, 9 H), 1.6 (d, J=3.4 Hz, 1 H), 1.6 (m, 1 H), 1.7 (m, 1 H), 2.0 (m, 1 H), 2.4 (m, 1 H), 2.8 (m, 1 H), 3.0 (s, 1 H), 3.7 (s, 3 H), 3.9 (d, J13.2 Hz, 1 H), 4.1 (s, 1 H).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-92547feaf7f44f27b6965639d1b5618b
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423054B2

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