Technology Process of (4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate
There total 1 articles about (4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(4S,5R)-4-methyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester;
With
N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine;
In
tetrahydrofuran;
at -85 - -78 ℃;
for 0.583333h;
Inert atmosphere;
1-iodo-4-pentene;
In
tetrahydrofuran;
at -78 - 20 ℃;
for 24.5h;
optical yield given as %de;
diastereoselective reaction;
Inert atmosphere;
DOI:10.1021/ol301461e
- Guidance literature:
-
(4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate;
With
N,O-dimethylhydroxylamine*hydrochloride;
In
tetrahydrofuran;
for 0.0833333h;
Inert atmosphere;
methylmagnesium bromide;
In
tetrahydrofuran;
at -5 - 20 ℃;
Inert atmosphere;
DOI:10.1021/ol301461e
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: N,O-dimethylhydroxylamine*hydrochloride / tetrahydrofuran / 0.08 h / Inert atmosphere
1.2: -5 - 20 °C / Inert atmosphere
2.1: ozone / ethyl acetate / -78 °C
2.2: 8 h / Inert atmosphere; Reflux
3.1: silica gel; N-ethyl-N,N-diisopropylamine / toluene / 48 h / 75 °C
4.1: 2,2'-azobis(isobutyronitrile); bromine; potassium carbonate / dichloromethane / 40 °C / Inert atmosphere
4.2: 60 °C
5.1: sodium tetrahydroborate / methanol
With
sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); bromine; N,O-dimethylhydroxylamine*hydrochloride; silica gel; potassium carbonate; ozone; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;
3.1: Aldol condensation;
DOI:10.1021/ol301461e
