Conversion of Nitriles into Tertiary Amines: N,N‐Dimethylhomoveratrylamine

Abstract

Conversion of nitriles into tertiary amines: N,N‐dimethylhomoveratrylamine intermediate: 2‐(3,4‐Dimethoxyphenyl)‐N,N‐dimethylacetamidine product: N,N‐dimethylhomoveratrylamine product: CH 3 CH 2 NH(CH 2 ) 5 CH 3 product: CH 3 CH 2 NHCH 2 C 6 H 5

Lissoclinotoxins E and F, Novel Cytotoxic Alkaloids from a Philippine Didemnid Ascidian.

“…An The structural relationship between compounds 1 and 2 was confirmed by desulfurization of a mixture of these metabolites using Raney Ni in MeOH at 90 C. 15,16 Purification of the reaction product by C 18 flash chromatography [MeOH/aqueous TFA (0.1%)] yielded the pure TFA salt of 2-(3,4-dimethoxyphenyl)-N,N-dimethylethanamine (3), which has been previously reported in the literature both as a synthetic compound 17,18 and as a natural product. [19][20][21] Although the gross structures for compounds 1 and 2 had been conclusively proven by spectroscopic and chemical degradation methods, the determination of stereochemistry about both tricyclic systems had not been established.…”

Photomediated asymmetric synthesis of (–)-cupareneElectronic supplementary information (ESI) available: experimental procedures and data including copies of 1H-NMR and 13C-NMR spectra for all new compounds, and NOESY spectra for compounds 9, 10, 11, 15 and 16. See http://www.rsc.org/suppdata/cc/b3/b300815k/

“…See http://www.rsc.org/suppdata/cc/b3/b300815k/ Alternatively, 8 could be prepared from 4-methylisobutyrophenone 5 via a three step sequence involving conjugate addition to acrylonitrile, Wittig reaction, and a one-pot reductive amination of nitrile 7 via an amidine intermediate. 6 Irradiation of 8 with a 400 W medium pressure mercury arc lamp in an immersion well reactor under high dilution conditions (0.005 M) cleanly gave a mixture of two cycloadducts in a 6+1 ratio as determined by integration of the 1 H-NMR spectrum of the crude reaction mixture. The combined yield of the two cycloadducts was 100%, and we were able to separate the major diastereomer 9 in 62% isolated yield by careful column chromatography.…”