methyl (S,S,E)-3-[n-allyl-N-(α-methyl-p-methoxybenzyl)amino]hept-5-enoate

Base Information

Chemical Name:methyl (S,S,E)-3-[n-allyl-N-(α-methyl-p-methoxybenzyl)amino]hept-5-enoate
CAS No.:1365993-54-9
Molecular Formula:C₂₀H₂₉NO₃
Molecular Weight:331.455
Hs Code.:

Synonyms:methyl (S,S,E)-3-[n-allyl-N-(α-methyl-p-methoxybenzyl)amino]hept-5-enoate

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Chemical Property of methyl (S,S,E)-3-[n-allyl-N-(α-methyl-p-methoxybenzyl)amino]hept-5-enoate

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Technology Process of methyl (S,S,E)-3-[n-allyl-N-(α-methyl-p-methoxybenzyl)amino]hept-5-enoate

There total 1 articles about methyl (S,S,E)-3-[n-allyl-N-(α-methyl-p-methoxybenzyl)amino]hept-5-enoate 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: 87.0%

: 18261-30-8,32793-92-3,32793-93-4,40415-88-1,41792-07-8
(E,E)-methyl heptan-2,5-dieneoate

: 953777-79-2
(S)-N-allyl-N-(α-methyl-p-methoxybenzyl)amine

: 1365993-54-9
methyl (S,S,E)-3-[n-allyl-N-(α-methyl-p-methoxybenzyl)amino]hept-5-enoate

Guidance literature:: (S)-N-allyl-N-(α-methyl-p-methoxybenzyl)amine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

(E,E)-methyl heptan-2,5-dieneoate; In tetrahydrofuran; at -78 ℃; for 2h; stereoselective reaction; Inert atmosphere;
DOI:10.1021/acs.orglett.7b00434

Reference yield:

: 1365993-54-9
methyl (S,S,E)-3-[n-allyl-N-(α-methyl-p-methoxybenzyl)amino]hept-5-enoate

: 1365993-61-8
(2R,4S,5R,Z)-1-tert-butoxycarbonyl-2-(6-benzyloxyhex-2-enyl)-4,5-epoxypiperidine

Guidance literature:: Multi-step reaction with 8 steps

1.1: triethylsilane; formic acid / 12 h / 90 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: sodium hydrogencarbonate / methanol / 12 h / 20 °C / Inert atmosphere; Sonication

3.1: Grubbs catalyst first generation / dichloromethane / 12 h / 20 °C / Inert atmosphere

4.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 12 h / 50 °C

4.2: pH 4

5.1: iodine; sodium hydrogencarbonate / acetonitrile / 12 h / -20 - 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.58 h / -78 °C / Inert atmosphere

6.2: 1 h / -78 - 20 °C / Inert atmosphere

7.1: sodium hydroxide / dichloromethane; water / 1 h / 20 °C / Inert atmosphere

8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.67 h / 0 - 20 °C / Inert atmosphere

8.2: 16 h / 0 - 20 °C / Inert atmosphere

With Grubbs catalyst first generation; triethylsilane; formic acid; lithium hydroxide monohydrate; iodine; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; 8.1: Wittig reaction / 8.2: Wittig reaction;
DOI:10.1021/ol300209s

Reference yield:

: 1365993-54-9
methyl (S,S,E)-3-[n-allyl-N-(α-methyl-p-methoxybenzyl)amino]hept-5-enoate

: 1365993-63-0
(2R,4S,5R)-1-tert-butoxycarbonyl-2-(6-[1-phenyl-1H-tetrazol-5-ylsulfanyl]hexyl)-4,5-epoxypiperidine

Guidance literature:: Multi-step reaction with 10 steps

1.1: triethylsilane; formic acid / 12 h / 90 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: sodium hydrogencarbonate / methanol / 12 h / 20 °C / Inert atmosphere; Sonication

3.1: Grubbs catalyst first generation / dichloromethane / 12 h / 20 °C / Inert atmosphere

4.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 12 h / 50 °C

4.2: pH 4

5.1: iodine; sodium hydrogencarbonate / acetonitrile / 12 h / -20 - 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.58 h / -78 °C / Inert atmosphere

6.2: 1 h / -78 - 20 °C / Inert atmosphere

7.1: sodium hydroxide / dichloromethane; water / 1 h / 20 °C / Inert atmosphere

8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.67 h / 0 - 20 °C / Inert atmosphere

8.2: 16 h / 0 - 20 °C / Inert atmosphere

9.1: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 2 h / 20 °C / 760.05 Torr

10.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

With Grubbs catalyst first generation; triethylsilane; formic acid; lithium hydroxide monohydrate; 20 % Pd(OH)2/C; hydrogen; iodine; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; acetonitrile; 8.1: Wittig reaction / 8.2: Wittig reaction / 10.1: Mitsunobu reaction;
DOI:10.1021/ol300209s