(4aR,7R,8aR)-tert-butyl 7-methyl-1-(4-methylphenylsulfonyl)-5-oxodecahydroquinoline-6-carboxylate

Base Information

Chemical Name:(4aR,7R,8aR)-tert-butyl 7-methyl-1-(4-methylphenylsulfonyl)-5-oxodecahydroquinoline-6-carboxylate
CAS No.:1416861-44-3
Molecular Formula:C₂₂H₃₁NO₅S
Molecular Weight:421.558
Hs Code.:

Synonyms:(4aR,7R,8aR)-tert-butyl 7-methyl-1-(4-methylphenylsulfonyl)-5-oxodecahydroquinoline-6-carboxylate

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Chemical Property of (4aR,7R,8aR)-tert-butyl 7-methyl-1-(4-methylphenylsulfonyl)-5-oxodecahydroquinoline-6-carboxylate

Chemical Property:

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Technology Process of (4aR,7R,8aR)-tert-butyl 7-methyl-1-(4-methylphenylsulfonyl)-5-oxodecahydroquinoline-6-carboxylate

There total 4 articles about (4aR,7R,8aR)-tert-butyl 7-methyl-1-(4-methylphenylsulfonyl)-5-oxodecahydroquinoline-6-carboxylate 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:

: 1416861-30-7
tert-butyl 7-(4-methylphenylsulfonamido)-3-oxoheptanoate

: 123-73-9,4170-30-3
crotonaldehyde

: 1416861-44-3
(4aR,7R,8aR)-tert-butyl 7-methyl-1-(4-methylphenylsulfonyl)-5-oxodecahydroquinoline-6-carboxylate

: 1416861-31-8
(4aS,7S,8aS)-tert-butyl 7-methyl-1-(4-methylphenylsulfonyl)-5-oxodecahydroquinoline-6-carboxylate

Guidance literature:: tert-butyl 7-(4-methylphenylsulfonamido)-3-oxoheptanoate; crotonaldehyde; With (L)-2-{diphenyl[(triphenylsilyl)oxy]methyl}pyrrolidine; In toluene; at 20 ℃; for 16h; Inert atmosphere;

With lithium hydroxide monohydrate; In water; isopropyl alcohol; for 24h; Reagent/catalyst; Solvent; enantioselective reaction;
DOI:10.1021/ol303257y

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 1416861-44-3
(4aR,7R,8aR)-tert-butyl 7-methyl-1-(4-methylphenylsulfonyl)-5-oxodecahydroquinoline-6-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydroxide / water / 3.25 h / Reflux

2.1: dibutylmagnesium / tetrahydrofuran; n-heptane / 1.25 h / -78 - 20 °C / Inert atmosphere

2.2: 1.25 h / 0 - 20 °C / Inert atmosphere

2.3: 20 °C / Inert atmosphere

3.1: C₃₅H₃₃NOSi; lithium acetate / toluene / 16 h / 0 °C / Inert atmosphere

3.2: 24 h

With C₃₅H₃₃NOSi; dibutylmagnesium; lithium acetate; sodium hydroxide; In tetrahydrofuran; n-heptane; water; toluene;
DOI:10.1021/ol303257y

Reference yield:

: 2042-45-7
5-(4-methylphenylsulfonamido)pentanoic acid

: 1416861-44-3
(4aR,7R,8aR)-tert-butyl 7-methyl-1-(4-methylphenylsulfonyl)-5-oxodecahydroquinoline-6-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: dibutylmagnesium / tetrahydrofuran; n-heptane / 1.25 h / -78 - 20 °C / Inert atmosphere

1.2: 1.25 h / 0 - 20 °C / Inert atmosphere

1.3: 20 °C / Inert atmosphere

2.1: C₃₅H₃₃NOSi; lithium acetate / toluene / 16 h / 0 °C / Inert atmosphere

2.2: 24 h

With C₃₅H₃₃NOSi; dibutylmagnesium; lithium acetate; In tetrahydrofuran; n-heptane; toluene;
DOI:10.1021/ol303257y