(5R,7S,8aS)-5-Benzyl-6-hydroxy-3,3,7-trimethyl-4-oxo-hexahydro-2-oxa-3a,6-diaza-azulene-7-carbonitrile

Base Information

Chemical Name:(5R,7S,8aS)-5-Benzyl-6-hydroxy-3,3,7-trimethyl-4-oxo-hexahydro-2-oxa-3a,6-diaza-azulene-7-carbonitrile
CAS No.:263871-10-9
Molecular Formula:C₁₈H₂₃N₃O₃
Molecular Weight:329.399
Hs Code.:

Synonyms:(5R,7S,8aS)-5-Benzyl-6-hydroxy-3,3,7-trimethyl-4-oxo-hexahydro-2-oxa-3a,6-diaza-azulene-7-carbonitrile

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Chemical Property of (5R,7S,8aS)-5-Benzyl-6-hydroxy-3,3,7-trimethyl-4-oxo-hexahydro-2-oxa-3a,6-diaza-azulene-7-carbonitrile

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Technology Process of (5R,7S,8aS)-5-Benzyl-6-hydroxy-3,3,7-trimethyl-4-oxo-hexahydro-2-oxa-3a,6-diaza-azulene-7-carbonitrile

There total 7 articles about (5R,7S,8aS)-5-Benzyl-6-hydroxy-3,3,7-trimethyl-4-oxo-hexahydro-2-oxa-3a,6-diaza-azulene-7-carbonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

: 263871-00-7
(5R,7S,8aS)-5-Benzyl-3,3,7-trimethyl-4-oxo-hexahydro-2-oxa-3a,6-diaza-azulene-7-carbonitrile

: 263871-10-9
(5R,7S,8aS)-5-Benzyl-6-hydroxy-3,3,7-trimethyl-4-oxo-hexahydro-2-oxa-3a,6-diaza-azulene-7-carbonitrile

Guidance literature:: With methyltrioxorhenium(VII); urea; at 40 ℃; for 0.25h;
DOI:10.1021/ja002556s

Reference yield:

: 263870-93-5
(2S)-2-amino-4-penten-1-ol

: 263871-10-9
(5R,7S,8aS)-5-Benzyl-6-hydroxy-3,3,7-trimethyl-4-oxo-hexahydro-2-oxa-3a,6-diaza-azulene-7-carbonitrile

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / tetrahydrofuran; methanol / 2 h / 0 °C

2: p-TsOH / toluene / 2 h / Heating

3: O₂; PdCl₂; CuCl / dimethylformamide; H₂O / 12 h / 20 °C

4: TMSOTf; 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

5: ZnCl₂ / propan-2-ol / 18 h / 20 °C

6: 87 percent / MeReO₃; aq. urea / 0.25 h / 40 °C

With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; oxygen; methyltrioxorhenium(VII); toluene-4-sulfonic acid; triethylamine; urea; copper(l) chloride; palladium dichloride; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 5: Strecker reaction;
DOI:10.1021/ja002556s

Reference yield:

: (5R,8aS)-5-Benzyl-3,3,7-trimethyl-1,5,8,8a-tetrahydro-2-oxa-3a,6-diaza-azulen-4-one

: 263871-10-9
(5R,7S,8aS)-5-Benzyl-6-hydroxy-3,3,7-trimethyl-4-oxo-hexahydro-2-oxa-3a,6-diaza-azulene-7-carbonitrile

Guidance literature:: Multi-step reaction with 2 steps

1: ZnCl₂ / propan-2-ol / 18 h / 20 °C

2: 87 percent / MeReO₃; aq. urea / 0.25 h / 40 °C

With methyltrioxorhenium(VII); urea; zinc(II) chloride; In isopropyl alcohol; 1: Strecker reaction;
DOI:10.1021/ja002556s