Multi-step reaction with 11 steps
1.1: lithium diisopropyl amide / n-heptane; benzene; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
1.2: 2.25 h / -40 °C
2.1: camphor-10-sulfonic acid / toluene / Dean-Stark system; Reflux
3.1: hydrogen / palladium 10% on activated carbon / methanol / 18 h / 20 °C / 760.05 Torr
4.1: hydrogenchloride; 2-amino-2-hydroxymethyl-1,3-propanediol; water; HLAP / 48 h / 40 °C / Enzymatic reaction
4.2: 20 °C / pH 3.5
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C / Inert atmosphere
5.2: 20 °C
6.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere
7.1: sodium iodide / acetonitrile / Inert atmosphere; Reflux
8.1: N,N-dimethyl acetamide / 24 h / 25 °C / Inert atmosphere
9.1: triethylamine / dmap / 3 h / Inert atmosphere
10.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere
11.1: triethylamine; hydrogen / (R)-(-)-4,12-bis(diphenylphosphino)[2.2]paracyclophane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate / ethanol / 6 h / 60 °C / 22502.3 Torr / Autoclave
With
hydrogenchloride; lithium aluminium tetrahydride; HLAP; water; hydrogen; triethylamine; 2-amino-2-hydroxymethyl-1,3-propanediol; trifluoroacetic acid; sodium iodide; lithium diisopropyl amide;
dmap; (R)-(-)-4,12-bis(diphenylphosphino)[2.2]paracyclophane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; palladium 10% on activated carbon; camphor-10-sulfonic acid;
In
tetrahydrofuran; methanol; ethanol; n-heptane; N,N-dimethyl acetamide; toluene; acetonitrile; benzene;