Technology Process of [(S)-1-(2-Bromo-3,5-dimethoxy-phenyl)-2-hydroxy-ethyl]-carbamic acid benzyl ester
There total 2 articles about [(S)-1-(2-Bromo-3,5-dimethoxy-phenyl)-2-hydroxy-ethyl]-carbamic acid benzyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
N-Bromosuccinimide;
In
acetonitrile;
at 0 ℃;
for 0.5h;
DOI:10.1021/ja992577q
- Guidance literature:
-
Multi-step reaction with 2 steps
1: (DHQ)2PHAL; K2Os2(OH)4; t-BuOCl / aq. NaOH; propan-1-ol / 0.5 h / 25 °C
2: NBS / acetonitrile / 0.5 h / 0 °C
With
potassium osmate; N-Bromosuccinimide; Hydroquinone 1,4-phthalazinediyl diether; tert-butylhypochlorite;
In
propan-1-ol; sodium hydroxide; acetonitrile;
1: asymmetric aminohydroxylation / 2: Bromination;
DOI:10.1021/ja992577q
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: i-Pr2NEt / CH2Cl2; tetrahydrofuran / 22 h / 25 °C
2.1: i-PrMgBr / 0.5 h / 0 °C
2.2: t-BuLi / -78 °C
2.3: 0.5 h / -78 - 0 °C
3.1: H20
4.1: Pd2(dba)3; (o-tolyl)3P; 1 N aq. Na2CO3 / methanol; toluene / 0.25 h / 80 °C
5.1: 96 percent / Bu4NF; AcOH / tetrahydrofuran / 6 h / 25 °C
6.1: 99 percent / 0.2 N aq. LiOH / tetrahydrofuran / 1 h / 0 °C
7.1: 80 percent / H2 / 10 percent Pd/C / ethanol; ethyl acetate / 11 h / 25 °C
With
lithium hydroxide; tris(dibenzylideneacetone)dipalladium (0); tetrabutyl ammonium fluoride; water; hydrogen; isopropylmagnesium bromide; sodium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; toluene;
1.1: Alkylation / 2.1: deprotonation / 2.2: Metallation / 2.3: Substitution / 3.1: Hydrolysis / 4.1: Suzuki coupling / 5.1: desilylation / 6.1: Hydrolysis / 7.1: Hydrogenolysis;
DOI:10.1021/ja992577q
