(5S)-11-ethylidene-7,8,9,10-tetrahydro-2-methoxy-7-methylene-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester

Base Information

Chemical Name:(5S)-11-ethylidene-7,8,9,10-tetrahydro-2-methoxy-7-methylene-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester
CAS No.:258522-29-1
Molecular Formula:C₂₉H₃₃NO₃
Molecular Weight:443.586
Hs Code.:

(5S)-11-ethylidene-7,8,9,10-tetrahydro-2-methoxy-7-methylene-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester

Synonyms:(5S)-11-ethylidene-7,8,9,10-tetrahydro-2-methoxy-7-methylene-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester

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Chemical Property of (5S)-11-ethylidene-7,8,9,10-tetrahydro-2-methoxy-7-methylene-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester

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Technology Process of (5S)-11-ethylidene-7,8,9,10-tetrahydro-2-methoxy-7-methylene-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester

There total 4 articles about (5S)-11-ethylidene-7,8,9,10-tetrahydro-2-methoxy-7-methylene-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester 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: 54.0%

: 1530-32-1
ethyltriphenylphosphonium bromide

: 258522-25-7
(5S)-7,8,9,10-tetrahydro-2-methoxy-7-methylene-11-oxo-5,9-methanocycloocta[b]pyridine-5(6H)carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester

: 258522-29-1
(5S)-11-ethylidene-7,8,9,10-tetrahydro-2-methoxy-7-methylene-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester

Guidance literature:: ethyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran;

(5S)-7,8,9,10-tetrahydro-2-methoxy-7-methylene-11-oxo-5,9-methanocycloocta[b]pyridine-5(6H)carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester; In tetrahydrofuran;
DOI:10.1016/S0040-4039(99)01874-2

Reference yield:

: 98919-68-7
(1R,2S)-trans-2-phenylcyclohexanol

: 258522-29-1
(5S)-11-ethylidene-7,8,9,10-tetrahydro-2-methoxy-7-methylene-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 81 percent / APTS / benzene / 48 h / Heating

2.1: Pd(PPh₃)4; 1,1,3,3-tetramethyl guanidine / dioxane / 18 h / 20 °C

3.1: t-BuOK / tetrahydrofuran

3.2: 54 percent / tetrahydrofuran

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium tert-butylate; 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; 1,4-dioxane; benzene; 1.1: Esterification / 2.1: bicycloannulation / 3.1: deprotonation / 3.2: Wittig reaction;
DOI:10.1016/S0040-4039(99)01874-2

Reference yield:

: 123435-97-2,130518-34-2
5,6,7,8-tetrahydro-2-methoxy-6-oxo-5-quinolinecarboxylic acid methyl ester

: 258522-29-1
(5S)-11-ethylidene-7,8,9,10-tetrahydro-2-methoxy-7-methylene-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 81 percent / APTS / benzene / 48 h / Heating

2.1: Pd(PPh₃)4; 1,1,3,3-tetramethyl guanidine / dioxane / 18 h / 20 °C

3.1: t-BuOK / tetrahydrofuran

3.2: 54 percent / tetrahydrofuran

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium tert-butylate; 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; 1,4-dioxane; benzene; 1.1: Esterification / 2.1: bicycloannulation / 3.1: deprotonation / 3.2: Wittig reaction;
DOI:10.1016/S0040-4039(99)01874-2