2,2,6,6-Tetramethylpiperidine

Chemical properties

clear colorless to light yellow-green liquid

The Uses of 2,2,6,6-Tetramethylpiperidine

2,2,6,6-Tetramethylpiperidine is used in the syntheses of HMP-Y1, Hibarimicinone and HMP-P1, tyrosine kinase inhibitors.

The Uses of 2,2,6,6-Tetramethylpiperidine

A mixture of the bromide (1.0 equiv), the organozinc bromide (0.5 M in THF, 2.0 equiv), and Pd(dppf)Cl2-DCM (0.2 equiv) in THF (0.1 M) was heated at 100 C for 20 min in a microwave reactor. Upon cooling, the solution was partitioned between EtOAc and sat aq Na2CO3. The org layer was separated and washed with brine, dried (MgSO4), concentrated, and purified by silica gel chromatography (20% EtOAc/hexane) to provide the product. [73%]

The Uses of 2,2,6,6-Tetramethylpiperidine

2,2,6,6-Tetramethylpiperidine is a hindered base used to prepare metallo-amide bases and selective generation of silylketene acetals. It is used in the preparation of hibarimicinone, (Z)-silylketene acetal and 4-substituted quinazoline. It acts as a precursor to Lithium tetramethylpiperidide and (2,2,6,6-Tetramethylpiperidin-1-yl)oxyl radical.

The Uses of 2,2,6,6-Tetramethylpiperidine

The lithium amide has been used to efficiently ortho deprotonate pyridine-3-carboxamides.

Preparation

Many routes for the synthesis of TMP have been reported. One method starts with a conjugate addition reaction of ammonia to phorone. The intermediate triacetone amine is then reduced in a Wolff-Kishner reaction.