Multi-step reaction with 8 steps
1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C
1.2: 3 h / 20 °C / Reflux
2.1: tetra-N-butylammonium tribromide / tetrahydrofuran; methanol / 4 h
3.1: borane N,N-diethylaniline complex; (1R,2S)-1-Amino-2-indanol / tetrahydrofuran / 3.5 h / 3 - 5 °C
4.1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 12 h / 20 - 25 °C / 5175.52 Torr
5.1: pyridine / tetrahydrofuran / 2 h / 20 °C
6.1: 1H-imidazole / dichloromethane / 1 h / Reflux
7.1: propiononitrile / 48 h / Reflux
8.1: triethylamine tris(hydrogen fluoride) / propiononitrile / 3 h / 25 °C
With
pyridine; 1H-imidazole; platinum(IV) oxide; borane N,N-diethylaniline complex; (1R,2S)-1-Amino-2-indanol; hydrogen; tetra-N-butylammonium tribromide; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; dichloromethane; acetonitrile; propiononitrile;
DOI:10.1021/op2001904