Technology Process of (1R,2S,5R,8S)-5-benzyl-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one
There total 9 articles about (1R,2S,5R,8S)-5-benzyl-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(1R,2S,8S)-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]-undec-6-en-4-one;
With
n-butyllithium; diisopropylamine;
In
tetrahydrofuran;
at -30 ℃;
for 1.5h;
benzyl bromide;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;
at -78 ℃;
for 10h;
Further stages.;
DOI:10.1021/jo011139a
- Guidance literature:
-
(1R,2S,8S)-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]-undec-6-en-4-one;
With
lithium diisopropyl amide;
In
tetrahydrofuran;
at -45 ℃;
for 0.166667h;
benzyl chloride;
In
tetrahydrofuran;
at -78 - -40 ℃;
stereoselective reaction;
DOI:10.1021/acs.orglett.7b02296
- Guidance literature:
-
Multi-step reaction with 2 steps
1.1: sodium borohydride / diethyl ether; methanol / 0.5 h / cooling
1.2: 4-(N,N-dimethylamino)pyridine; dicyclohexylcarbodiimide / tetrahydrofuran / 18 h / 0 - 20 °C
1.3: 0.78 g / H2 / Pd/C / ethanol / 14 h / 25 °C / 760 Torr
2.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 1.5 h / -30 °C
2.2: hexamethylphosphoric triamide / tetrahydrofuran; hexane / -78 °C
2.3: tetrahydrofuran; hexane / 12 h / -78 °C
With
sodium tetrahydroborate; n-butyllithium; diisopropylamine;
In
tetrahydrofuran; methanol; diethyl ether; hexane;
DOI:10.1021/jo052435g
