DBU

Description

DBU is considered to be a non-nucleophilic base. DBU can serve as a base, catalyst, or complexing ligand in a wide variety of reactions.

Occurrence

Although all commercially available DBU is produced synthetically, it may also be isolated from the sea sponge Niphates digitalis.The biosynthesis of DBU has been proposed to begin with 1,6-hexanedial and 1,3-diaminopropane. 

The Uses of DBU

To a suspension of the SM (0.665 g, 1.66 mmol) in THF (10 mL) at RT under Ar was added DPPA (0.400 mL, 1.83 mmol) and DBU (0.297 mL, 1.99 mmol). The resulting mixture was stirred at RT for 18 h. Additional DPPA (0.200 mL, 0.916 mmol) and DBU (0.150 mL, 1.00 mmol) was added and the mixture was stirred at RT for 3 h. The reaction mixture was quenched with sat aq NaHCO3 (30 mL). The aq mixture was extracted EtOAc (2 x 30 mL). The combined organics were dried (Na2SO4) and concentrated to a yellow gum. The material (1.26 g) was purified by Prep LC (2-5% MeOH/DCM) to provide the product as an off-white solid. [370 mg, 52%]

General Description

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Reactions

DBU is a less expensive and readily available base in most of the synthetic laboratories has low nucleophilicity. The presence of adjacent nitrogen atoms is believed to stabilize the protonated species during its basic action.

Synthesis

DBU can be synthesized from a lactam, azepan-2-one. N-Cyanoethylation of lactam is carried out using acrylonitrile in the presence of a potassium hydroxide as base to produce the nitrite, which is reduced using Raney-nickel in the presence of NH3to give N-(3-aminopropyl)-azepan-2-one. Then further undergoes condensation in the presence of p-toluenesulphonic acid (p-TSA) to yield DBU.