Reaction #2358538

ord-539bbd52ae5e44098e3a30be38d62910

Reaction equation

CC(CO)NC(=O)c1cccc(C#CCC(C)C(=O)N(C)C)c1
alkyne
CC(CO)NC(=O)c1cccc(C#CCC(C)C(=O)N(C)C)c1
3-(4-Dimethylcarbamoyl-pent-1-ynyl)-N-(2-hydroxy-1-methyl-ethyl)benzamide
→
CC(CO)NC(=O)c1cccc(C=CCCC(=O)N(C)C)c1
27
Yield 40.0%
CC(CO)NC(=O)c1cccc(C=CCCC(=O)N(C)C)c1
3-(4-Dimethylcarbamoyl-but-1-enyl)-N-(2-hydroxy-1-methyl-ethyl)-benzamide
Yield 40.0%

Reactants

CC(CO)NC(=O)c1cccc(C#CCC(C)C(=O)N(C)C)c1
alkyne
CC(CO)NC(=O)c1cccc(C#CCC(C)C(=O)N(C)C)c1
3-(4-Dimethylcarbamoyl-pent-1-ynyl)-N-(2-hydroxy-1-methyl-ethyl)benzamide

Reagents

[Ni]
Ni

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Hydrogenation of the alkyne 9 (0.055 g, 0.18 mmol) using BER/Ni catalyst gave 40% 27, 5% of the saturated compound and 55% of starting material. The mixture was separated by reverse-phase HPLC chromatography (20% acetonitrile/80% water 20 min isocratic program) to give 27 (15 mg).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09120723B2uspto-grants-2015_09