(rac)-allyl 3-(2-ethoxy-2-oxoethyl)-4-oxo-9-tosyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate

Base Information

Chemical Name:(rac)-allyl 3-(2-ethoxy-2-oxoethyl)-4-oxo-9-tosyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate
CAS No.:1451144-23-2
Molecular Formula:C₂₇H₂₇NO₇S
Molecular Weight:509.58
Hs Code.:

Synonyms:(rac)-allyl 3-(2-ethoxy-2-oxoethyl)-4-oxo-9-tosyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate

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Chemical Property of (rac)-allyl 3-(2-ethoxy-2-oxoethyl)-4-oxo-9-tosyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate

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Technology Process of (rac)-allyl 3-(2-ethoxy-2-oxoethyl)-4-oxo-9-tosyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate

There total 2 articles about (rac)-allyl 3-(2-ethoxy-2-oxoethyl)-4-oxo-9-tosyl-2,3,4,9-tetrahydro-1H-carbazole-3-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: 68.0%

: 1451144-20-9
allyl 4-oxo-9-tosyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate

: 1451144-23-2
(rac)-allyl 3-(2-ethoxy-2-oxoethyl)-4-oxo-9-tosyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate

Guidance literature:: allyl 4-oxo-9-tosyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.333333h;

ethyl halidoacetate; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 2h;
DOI:10.1071/CH13287

Reference yield:

: 1451144-16-3
allyl 4-oxo-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate

: 1451144-23-2
(rac)-allyl 3-(2-ethoxy-2-oxoethyl)-4-oxo-9-tosyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 3 h / 0 °C

2.1: sodium hydride / mineral oil; tetrahydrofuran / 0.33 h / 0 °C

2.2: 2 h / 0 - 20 °C

With tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; sodium hydroxide; In tetrahydrofuran; dichloromethane; water; mineral oil;
DOI:10.1071/CH13287

Reference yield:

: 1451144-23-2
(rac)-allyl 3-(2-ethoxy-2-oxoethyl)-4-oxo-9-tosyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate

: 1451144-34-5
(S)-ethyl 2-(3-allyl-4-oxo-9-tosyl-2,3,4,9-tetrahydro-1H-carbazol-3-yl)acetate

: (R)-ethyl 2-(3-allyl-4-oxo-9-tosyl-2,3,4,9-tetrahydro-1H-carbazol-3-yl)acetate

Guidance literature:: With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (4S)-2-[2-(diphenylphosphino)phenyl]-4-isopropyl-4,5-dihydro-1,3-oxazole; In toluene; at 80 ℃; for 4h; Overall yield = 98 %; enantioselective reaction; Inert atmosphere;
DOI:10.1002/anie.201209069