(1S)-N-(8-menthyl)-1-(benzyloxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Base Information

Chemical Name:(1S)-N-(8-menthyl)-1-(benzyloxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
CAS No.:321670-09-1
Molecular Formula:C₂₉H₄₁NO₄
Molecular Weight:467.649
Hs Code.:

Synonyms:(1S)-N-(8-menthyl)-1-(benzyloxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

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Chemical Property of (1S)-N-(8-menthyl)-1-(benzyloxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

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Technology Process of (1S)-N-(8-menthyl)-1-(benzyloxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

There total 6 articles about (1S)-N-(8-menthyl)-1-(benzyloxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 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: 77.0%

: 321669-86-7
2α-benzyloxymethyl-3-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine

: 321670-09-1
(1S)-N-(8-menthyl)-1-(benzyloxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: 2α-benzyloxymethyl-3-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine; With tert.-butyl lithium; In diethyl ether; pentane; at -90 ℃; for 0.166667h;

With diethylaluminium chloride; In hexane; at -90 - 20 ℃; Further stages.;
DOI:10.1021/jo001397s

Reference yield:

: 55171-60-3
2-bromo-3,4-dimethoxybenzylaldehyde

: 321670-09-1
(1S)-N-(8-menthyl)-1-(benzyloxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium tert-butoxide / tetrahydrofuran / 0.5 h / 0 °C

1.2: tetrahydrofuran / 12 h / 20 °C

1.3: 90 percent / formic acid / CH₂Cl₂ / 72 h / 20 °C

2.1: 95 percent / CH₂Cl₂ / 20 °C

3.1: NaBH₄; BF₃*OEt₂ / tetrahydrofuran / 2 h / 20 °C

3.2: 90 percent / NaOH / H₂O / 1 h / Heating

4.1: 90 percent / 120 °C

5.1: t-BuLi / diethyl ether; pentane / 0.17 h / -90 °C

5.2: 77 percent / Et₂AlCl / hexane / -90 - 20 °C

With sodium tetrahydroborate; boron trifluoride diethyl etherate; potassium tert-butylate; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;
DOI:10.1021/jo001397s

Reference yield:

: 60656-87-3
benzyloxyacetoaldehyde

: 321670-09-1
(1S)-N-(8-menthyl)-1-(benzyloxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: Multi-step reaction with 2 steps

1.1: 90 percent / 120 °C

2.1: t-BuLi / diethyl ether; pentane / 0.17 h / -90 °C

2.2: 77 percent / Et₂AlCl / hexane / -90 - 20 °C

With tert.-butyl lithium; In diethyl ether; pentane;
DOI:10.1021/jo001397s