(S)-benzyl 5-allyl-5-[(S)-1-hydroxybut-3-enyl]-5,6-dihydropyridine-1(2H)-carboxylate

Base Information

Chemical Name:(S)-benzyl 5-allyl-5-[(S)-1-hydroxybut-3-enyl]-5,6-dihydropyridine-1(2H)-carboxylate
CAS No.:1356215-12-7
Molecular Formula:C₂₀H₂₅NO₃
Molecular Weight:327.423
Hs Code.:

Synonyms:(S)-benzyl 5-allyl-5-[(S)-1-hydroxybut-3-enyl]-5,6-dihydropyridine-1(2H)-carboxylate

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Chemical Property of (S)-benzyl 5-allyl-5-[(S)-1-hydroxybut-3-enyl]-5,6-dihydropyridine-1(2H)-carboxylate

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Technology Process of (S)-benzyl 5-allyl-5-[(S)-1-hydroxybut-3-enyl]-5,6-dihydropyridine-1(2H)-carboxylate

There total 4 articles about (S)-benzyl 5-allyl-5-[(S)-1-hydroxybut-3-enyl]-5,6-dihydropyridine-1(2H)-carboxylate 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:

: 1356215-16-1
(S)-benzyl 5-allyl-5-formyl-5,6-dihydropyridine-1(2H)-carboxylate

: 762-72-1
allyl-trimethyl-silane

: 1356215-49-0
(S)-benzyl 5-allyl-5-[(R)-1-hydroxybut-3-enyl]-5,6-dihydropyridine-1(2H)-carboxylate

: 1356215-12-7
(S)-benzyl 5-allyl-5-[(S)-1-hydroxybut-3-enyl]-5,6-dihydropyridine-1(2H)-carboxylate

Guidance literature:: (S)-benzyl 5-allyl-5-formyl-5,6-dihydropyridine-1(2H)-carboxylate; With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 0.25h; Inert atmosphere;

allyl-trimethyl-silane; In dichloromethane; at -78 ℃; for 6h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201101256

Reference yield:

: 1320327-46-5
(S)-methyl 3-allyl-2-oxo-1,2,3,6-tetrahydropyridine-3-carboxylate

: 1356215-49-0
(S)-benzyl 5-allyl-5-[(R)-1-hydroxybut-3-enyl]-5,6-dihydropyridine-1(2H)-carboxylate

: 1356215-12-7
(S)-benzyl 5-allyl-5-[(S)-1-hydroxybut-3-enyl]-5,6-dihydropyridine-1(2H)-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / ethanol / 48 h / 20 °C

2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 5 h / 0 - 20 °C

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 8 h / Reflux

4.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

4.2: 6 h / -78 °C / Inert atmosphere

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; boron trifluoride diethyl etherate; sodium hydrogencarbonate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate; 4.1: Hosomi-Hosomi-Sakurai allylation / 4.2: Hosomi-Sakurai allylation;
DOI:10.1002/ejoc.201101256

Reference yield:

: 1356215-51-4
(R)-3-allyl-3-(hydroxymethyl)-1,6-dihydropyridin-2(3H)-one

: 1356215-49-0
(S)-benzyl 5-allyl-5-[(R)-1-hydroxybut-3-enyl]-5,6-dihydropyridine-1(2H)-carboxylate

: 1356215-12-7
(S)-benzyl 5-allyl-5-[(S)-1-hydroxybut-3-enyl]-5,6-dihydropyridine-1(2H)-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydrogencarbonate / 1,4-dioxane; water / 5 h / 0 - 20 °C

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 8 h / Reflux

3.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

3.2: 6 h / -78 °C / Inert atmosphere

With boron trifluoride diethyl etherate; sodium hydrogencarbonate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In 1,4-dioxane; dichloromethane; water; ethyl acetate; 3.1: Hosomi-Hosomi-Sakurai allylation / 3.2: Hosomi-Sakurai allylation;
DOI:10.1002/ejoc.201101256