(1S,5R,6R)-2-allyl-6-(benzyloxy)-3-(4-methoxybenzyl)-1-vinyl-2-azabicyclo[3.3.1]non-3-ene

Base Information

Chemical Name:(1S,5R,6R)-2-allyl-6-(benzyloxy)-3-(4-methoxybenzyl)-1-vinyl-2-azabicyclo[3.3.1]non-3-ene
CAS No.:1416404-29-9
Molecular Formula:C₂₈H₃₃NO₂
Molecular Weight:415.576
Hs Code.:

Synonyms:(1S,5R,6R)-2-allyl-6-(benzyloxy)-3-(4-methoxybenzyl)-1-vinyl-2-azabicyclo[3.3.1]non-3-ene

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Chemical Property of (1S,5R,6R)-2-allyl-6-(benzyloxy)-3-(4-methoxybenzyl)-1-vinyl-2-azabicyclo[3.3.1]non-3-ene

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Technology Process of (1S,5R,6R)-2-allyl-6-(benzyloxy)-3-(4-methoxybenzyl)-1-vinyl-2-azabicyclo[3.3.1]non-3-ene

There total 10 articles about (1S,5R,6R)-2-allyl-6-(benzyloxy)-3-(4-methoxybenzyl)-1-vinyl-2-azabicyclo[3.3.1]non-3-ene 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: 94.0%

: 1416404-28-8
(1S,3S,5S,6R)-2-allyl-6-(benzyloxy)-3-(4-methoxybenzyl)-1-vinyl-2-azabicyclo[3.3.1]nonan-4-one

: 1416404-29-9
(1S,5R,6R)-2-allyl-6-(benzyloxy)-3-(4-methoxybenzyl)-1-vinyl-2-azabicyclo[3.3.1]non-3-ene

Guidance literature:: With samarium diiodide; water; In tetrahydrofuran; at 20 ℃; for 0.0833333h;
DOI:10.1021/jo302362b

Reference yield:

: 1395687-54-3
(R)-1-allyl-5-(benzyloxy)piperidin-2-one

: 1416404-29-9
(1S,5R,6R)-2-allyl-6-(benzyloxy)-3-(4-methoxybenzyl)-1-vinyl-2-azabicyclo[3.3.1]non-3-ene

Guidance literature:: Multi-step reaction with 8 steps

1.1: trifluoromethylsulfonic anhydride; 2,6-di-tert-butyl-4-methylpyridine / dichloromethane

2.1: lithium naphthalenide / tetrahydrofuran / 1 h / -40 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

4.1: hydrogenchloride / tetrahydrofuran; water / 1.5 h / 20 - 50 °C

4.3: CSA / 0.17 h / 90 °C

5.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 18 h / 20 °C

6.1: hydrogenchloride / acetone / 24 h / Reflux

7.1: N,N,N,N,-tetramethylethylenediamine; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C

7.2: -78 - 0 °C

8.1: water; samarium diiodide / tetrahydrofuran / 0.08 h / 20 °C

With hydrogenchloride; 2,6-di-tert-butyl-4-methylpyridine; samarium diiodide; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; trifluoromethylsulfonic anhydride; water; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;
DOI:10.1021/jo302362b

Reference yield:

: 1395687-62-3
(2R,5R)-2-[2-(1,3-dioxolan-2-yl)ethyl]-1-allyl-5-(benzyloxy)-2-vinylpiperidine

: 1416404-29-9
(1S,5R,6R)-2-allyl-6-(benzyloxy)-3-(4-methoxybenzyl)-1-vinyl-2-azabicyclo[3.3.1]non-3-ene

Guidance literature:: Multi-step reaction with 7 steps

1.1: lithium naphthalenide / tetrahydrofuran / 1 h / -40 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

3.1: hydrogenchloride / tetrahydrofuran; water / 1.5 h / 20 - 50 °C

3.3: CSA / 0.17 h / 90 °C

4.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 18 h / 20 °C

5.1: hydrogenchloride / acetone / 24 h / Reflux

6.1: N,N,N,N,-tetramethylethylenediamine; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C

6.2: -78 - 0 °C

7.1: water; samarium diiodide / tetrahydrofuran / 0.08 h / 20 °C

With hydrogenchloride; samarium diiodide; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; water; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;
DOI:10.1021/jo302362b