(4aR,5S,6R)-5,6-Epoxy-2,3,7,8-tetrahydro-4H-4a-(benzyloxycarbonyl)quinoline

Base Information

Chemical Name:(4aR,5S,6R)-5,6-Epoxy-2,3,7,8-tetrahydro-4H-4a-(benzyloxycarbonyl)quinoline
CAS No.:171523-78-7
Molecular Formula:C₁₇H₁₉NO₃
Molecular Weight:285.343
Hs Code.:

Synonyms:(4aR,5S,6R)-5,6-Epoxy-2,3,7,8-tetrahydro-4H-4a-(benzyloxycarbonyl)quinoline

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4aR,5S,6R)-5,6-Epoxy-2,3,7,8-tetrahydro-4H-4a-(benzyloxycarbonyl)quinoline

Chemical Property:

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Technology Process of (4aR,5S,6R)-5,6-Epoxy-2,3,7,8-tetrahydro-4H-4a-(benzyloxycarbonyl)quinoline

There total 4 articles about (4aR,5S,6R)-5,6-Epoxy-2,3,7,8-tetrahydro-4H-4a-(benzyloxycarbonyl)quinoline 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: 84.0%

: 171523-75-4
(4aR,5R,6R)-5-Iodo-2,3,7,8-tetrahydro-4H-quinoline-4a,6-carbolactone

: 100-51-6,185532-71-2
benzyl alcohol

: 171523-78-7
(4aR,5S,6R)-5,6-Epoxy-2,3,7,8-tetrahydro-4H-4a-(benzyloxycarbonyl)quinoline

Guidance literature:: With n-butyllithium; In tetrahydrofuran; 1.) 0 deg C, 15 min., 2.) - 78 deg to r.t., overnight;
DOI:10.1021/jo00129a052

Reference yield:

: 171523-74-3
(2R,3R,4R)-1-Oxo-2-(3-azidopropyl)-3-iodocyclohexane-2,4-carbolactone

: 171523-78-7
(4aR,5S,6R)-5,6-Epoxy-2,3,7,8-tetrahydro-4H-4a-(benzyloxycarbonyl)quinoline

Guidance literature:: Multi-step reaction with 2 steps

1: 60 percent / SnCl₂, NaHCO₃ / dioxane; H₂O / 1.) 7 h, room temp., 2.) 45 min.

2: 84 percent / n-BuLi / tetrahydrofuran / 1.) 0 deg C, 15 min., 2.) - 78 deg to r.t., overnight

With n-butyllithium; sodium hydrogencarbonate; tin(ll) chloride; In tetrahydrofuran; 1,4-dioxane; water;
DOI:10.1021/jo00129a052

Reference yield:

: 171523-73-2
(R)-2-(3-Azido-propyl)-2-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-cyclohex-3-enone

: 171523-78-7
(4aR,5S,6R)-5,6-Epoxy-2,3,7,8-tetrahydro-4H-4a-(benzyloxycarbonyl)quinoline

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / I₂ / tetrahydrofuran; H₂O / 24 h / Ambient temperature

2: 60 percent / SnCl₂, NaHCO₃ / dioxane; H₂O / 1.) 7 h, room temp., 2.) 45 min.

3: 84 percent / n-BuLi / tetrahydrofuran / 1.) 0 deg C, 15 min., 2.) - 78 deg to r.t., overnight

With n-butyllithium; iodine; sodium hydrogencarbonate; tin(ll) chloride; In tetrahydrofuran; 1,4-dioxane; water;
DOI:10.1021/jo00129a052