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

HRID 1723841Notes

Reaction equation

HRID 1723841 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 235906521-tert-Butyl 3-methyl piperidine-1,3-dicarboxylateYield 83.7%

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

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).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-370f795a58284cb2b915c4aff436f940
Source dataset
uspto-grants-2009_02
Patent number
US07485636B2

Reaction notes

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