(+)-(1S,4S)-8-methoxy-1-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-1,4-methanobenzo[d]azepine

Base Information

Chemical Name:(+)-(1S,4S)-8-methoxy-1-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-1,4-methanobenzo[d]azepine
CAS No.:1308799-08-7
Molecular Formula:C₂₀H₂₃NO₃S
Molecular Weight:357.474
Hs Code.:

Synonyms:(+)-(1S,4S)-8-methoxy-1-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-1,4-methanobenzo[d]azepine

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Chemical Property of (+)-(1S,4S)-8-methoxy-1-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-1,4-methanobenzo[d]azepine

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Technology Process of (+)-(1S,4S)-8-methoxy-1-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-1,4-methanobenzo[d]azepine

There total 5 articles about (+)-(1S,4S)-8-methoxy-1-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-1,4-methanobenzo[d]azepine 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:

: 1308799-06-5
(+)-(5S)-5-(4-methoxybenzyl)-3-methyl-1-tosylpyrrolidin-3-ol

: 1308799-08-7
(+)-(1S,4S)-8-methoxy-1-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-1,4-methanobenzo[d]azepine

: 620163-17-9
(1R,4S)-1-methyl-8-methoxy-3-(4-toluenesulfonyl)-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine

Guidance literature:: With aluminum (III) chloride; In dichloromethane; at 0 - 20 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1021/ol2009895

Reference yield:

: 1308799-03-2
(+/-)-tert-butyl (2-hydroxy-2-methylpent-4-en-1-yl)carbamate

: 1308799-08-7
(+)-(1S,4S)-8-methoxy-1-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-1,4-methanobenzo[d]azepine

: 620163-17-9
(1R,4S)-1-methyl-8-methoxy-3-(4-toluenesulfonyl)-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine

Guidance literature:: Multi-step reaction with 5 steps

1: 4 h / 20 °C / Inert atmosphere

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (11aR)-(+)-10,11,12,13-tetrahydrodiindeno-[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine; sodium t-butanolate / toluene / 14 h / 20 - 90 °C / Inert atmosphere

3: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

4: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

5: aluminum (III) chloride / dichloromethane / 0 - 20 °C / Inert atmosphere

With aluminum (III) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (11aR)-(+)-10,11,12,13-tetrahydrodiindeno-[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine; triethylamine; trifluoroacetic acid; sodium t-butanolate; In tetrahydrofuran; dichloromethane; toluene; 5: Friedel Crafts alkylation;
DOI:10.1021/ol2009895

Reference yield:

: 1308799-00-9
(+/-)-tert-butyl {2-methyl-2-[(trimethylsilyl)oxy]pent-4-en-1-yl}carbamate

: 1308799-08-7
(+)-(1S,4S)-8-methoxy-1-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-1,4-methanobenzo[d]azepine

: 620163-17-9
(1R,4S)-1-methyl-8-methoxy-3-(4-toluenesulfonyl)-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine

Guidance literature:: Multi-step reaction with 4 steps

1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (11aR)-(+)-10,11,12,13-tetrahydrodiindeno-[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine; sodium t-butanolate / toluene / 14 h / 20 - 90 °C / Inert atmosphere

2: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

3: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

4: aluminum (III) chloride / dichloromethane / 0 - 20 °C / Inert atmosphere

With aluminum (III) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (11aR)-(+)-10,11,12,13-tetrahydrodiindeno-[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine; triethylamine; trifluoroacetic acid; sodium t-butanolate; In tetrahydrofuran; dichloromethane; toluene; 4: Friedel Crafts alkylation;
DOI:10.1021/ol2009895