cis-N-(p-methoxybenzyl)-3-methoxy-3,4-dihydrospiro[[2]benzopyran-1,1'-cyclohexan]-4'-amine

Base Information

Chemical Name:cis-N-(p-methoxybenzyl)-3-methoxy-3,4-dihydrospiro[[2]benzopyran-1,1'-cyclohexan]-4'-amine
CAS No.:1310743-79-3
Molecular Formula:C₂₃H₂₉NO₃
Molecular Weight:367.488
Hs Code.:

Synonyms:cis-N-(p-methoxybenzyl)-3-methoxy-3,4-dihydrospiro[[2]benzopyran-1,1'-cyclohexan]-4'-amine

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Chemical Property of cis-N-(p-methoxybenzyl)-3-methoxy-3,4-dihydrospiro[[2]benzopyran-1,1'-cyclohexan]-4'-amine

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Technology Process of cis-N-(p-methoxybenzyl)-3-methoxy-3,4-dihydrospiro[[2]benzopyran-1,1'-cyclohexan]-4'-amine

There total 5 articles about cis-N-(p-methoxybenzyl)-3-methoxy-3,4-dihydrospiro[[2]benzopyran-1,1'-cyclohexan]-4'-amine 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: 23.0%

: 1310743-77-1
3-methoxy-3,4-dihydrospiro[[2]benzopyran-1,1'-cyclohexan]-4'-one

: 2393-23-9
4-methoxy-benzylamine

: 1310743-79-3
cis-N-(p-methoxybenzyl)-3-methoxy-3,4-dihydrospiro[[2]benzopyran-1,1'-cyclohexan]-4'-amine

: 1311266-86-0
trans-N-(p-methoxybenzyl)-3-methoxy-3,4-dihydrospiro[[2]benzopyran-1,1'-cyclohexan]-4'-amine

Guidance literature:: With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; at 20 ℃; for 2.5h; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.bmc.2011.04.002

Reference yield:

: 130089-19-9,130089-23-5,59436-11-2
1-bromo-2-(2-methoxyethenyl)benzene

: 1310743-79-3
cis-N-(p-methoxybenzyl)-3-methoxy-3,4-dihydrospiro[[2]benzopyran-1,1'-cyclohexan]-4'-amine

: 1311266-86-0
trans-N-(p-methoxybenzyl)-3-methoxy-3,4-dihydrospiro[[2]benzopyran-1,1'-cyclohexan]-4'-amine

Guidance literature:: Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / 72 h / Reflux

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 - 20 °C / Inert atmosphere

3.1: hydrogenchloride / chloroform; water / 1.33 h / 20 °C

4.1: sodium tris(acetoxy)borohydride; acetic acid / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; sodium tris(acetoxy)borohydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; hexane; chloroform; water;
DOI:10.1016/j.bmc.2011.04.002

Reference yield:

: 6630-33-7
ortho-bromobenzaldehyde

: 1310743-79-3
cis-N-(p-methoxybenzyl)-3-methoxy-3,4-dihydrospiro[[2]benzopyran-1,1'-cyclohexan]-4'-amine

: 1311266-86-0
trans-N-(p-methoxybenzyl)-3-methoxy-3,4-dihydrospiro[[2]benzopyran-1,1'-cyclohexan]-4'-amine

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium tert-butylate / tetrahydrofuran / 16 h / -10 - 20 °C

2.1: toluene-4-sulfonic acid / 72 h / Reflux

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere

3.2: 3 h / -78 - 20 °C / Inert atmosphere

4.1: hydrogenchloride / chloroform; water / 1.33 h / 20 °C

5.1: sodium tris(acetoxy)borohydride; acetic acid / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; potassium tert-butylate; sodium tris(acetoxy)borohydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; hexane; chloroform; water; 1.1: Wittig reaction;
DOI:10.1016/j.bmc.2011.04.002