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

Base Information

Chemical Name:(2R,5R)-2-[2-(1,3-dioxolan-2-yl)ethyl]-1-allyl-5-(benzyloxy)-2-vinylpiperidine
CAS No.:1395687-62-3
Molecular Formula:C₂₂H₃₁NO₃
Molecular Weight:357.493
Hs Code.:

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

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Chemical Property of (2R,5R)-2-[2-(1,3-dioxolan-2-yl)ethyl]-1-allyl-5-(benzyloxy)-2-vinylpiperidine

Chemical Property:

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Technology Process of (2R,5R)-2-[2-(1,3-dioxolan-2-yl)ethyl]-1-allyl-5-(benzyloxy)-2-vinylpiperidine

There total 2 articles about (2R,5R)-2-[2-(1,3-dioxolan-2-yl)ethyl]-1-allyl-5-(benzyloxy)-2-vinylpiperidine 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:

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

: 1826-67-1
vinyl magnesium bromide

: 37610-80-3
1,3-dioxolan-2-ylethylmagnesium bromide

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

: 1395688-72-8
(2S,5R)-2-[2-(1,3-dioxolan-2-yl)ethyl]-1-allyl-5-(benzyloxy)-2-vinylpiperidine

Guidance literature:: (R)-1-allyl-5-(benzyloxy)piperidin-2-one; With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -78 ℃;

1,3-dioxolan-2-ylethylmagnesium bromide; In tetrahydrofuran; dichloromethane; at -78 ℃; for 2h;

vinyl magnesium bromide; In tetrahydrofuran; dichloromethane; at -78 - 20 ℃; Overall yield = 75 %; Overall yield = 2.68 g; diastereoselective reaction;
DOI:10.1021/ol302165d

Reference yield:

: 1254985-48-2
(R)-1-allyl-3-benzyloxy-2,6-piperidinedione

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

: 1395688-72-8
(2S,5R)-2-[2-(1,3-dioxolan-2-yl)ethyl]-1-allyl-5-(benzyloxy)-2-vinylpiperidine

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium tetrahydroborate / tetrahydrofuran / 0.25 h / -30 °C

1.2: -78 - 20 °C / Inert atmosphere

2.1: 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / -78 °C

2.2: 2 h / -78 °C

2.3: -78 - 20 °C

With sodium tetrahydroborate; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol302165d

Reference yield:

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

: 1416404-27-7
(1S,5S,6R)-2-allyl-6-(benzyloxy)-1-vinyl-2-azabicyclo[3.3.1]nonan-4-one

Guidance literature:: Multi-step reaction with 5 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

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