tert-butyl (3S,9aR)-3-(4-cyano-3-methoxyphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Base Information

• Chemical Name: tert-butyl (3S,9aR)-3-(4-cyano-3-methoxyphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate
• CAS No.: 1426072-37-8
• Molecular Formula: C₂₀H₂₇N₃O₄
• Molecular Weight: 373.452

Synonyms:tert-butyl (3S,9aR)-3-(4-cyano-3-methoxyphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Chemical Property of tert-butyl (3S,9aR)-3-(4-cyano-3-methoxyphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of tert-butyl (3S,9aR)-3-(4-cyano-3-methoxyphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

There total 12 articles about tert-butyl (3S,9aR)-3-(4-cyano-3-methoxyphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-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:

(R)-tert-butyl 3-(hydroxymethyl)piperazine-1-carboxylate (278788-66-2) → tert-butyl (3S,9aR)-3-(4-cyano-3-methoxyphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate (1426072-37-8) + tert-butyl (3R,9aR)-3-(4-cyano-3-methoxyphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate (1426072-38-9)

Guidance literature:

Multi-step reaction with 3 steps

1: ethanol / 3 h / 150 °C / Microwave irradiation

2: cyanomethylenetributyl-phosphorane / benzene / 3 h / 135 °C / Microwave irradiation

3: ChiralCel OJ-H / methanol / 75007.5 Torr

With cyanomethylenetributyl-phosphorane; In methanol; ethanol; benzene;

Reference yield:

(R)-tert-butyl 3-(hydroxymethyl)piperazine-1-carboxylate (278788-66-2) + 2-(methyloxy)-4-oxiran-2-ylbenzonitrile (1255207-21-6) → tert-butyl (3S,9aR)-3-(4-cyano-3-methoxyphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate (1426072-37-8) + tert-butyl (3R,9aR)-3-(4-cyano-3-methoxyphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate (1426072-38-9)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol / 3 h / 150 °C / Microwave irradiation

2: cyanomethylenetributyl-phosphorane / benzene / 3 h / 135 °C / Microwave irradiation

With cyanomethylenetributyl-phosphorane; In ethanol; benzene;

Reference yield:

tert-butyl (9aR)-3-(4-cyano-3-methoxyphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate → tert-butyl (3S,9aR)-3-(4-cyano-3-methoxyphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate (1426072-37-8) + tert-butyl (3R,9aR)-3-(4-cyano-3-methoxyphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate (1426072-38-9)

Guidance literature:

With ChiralCel OJ-H; In methanol; Supercritical conditions; Resolution of racemate;

upstream raw materials:

tert-butyl (3R)-4-[2-(4-cyano-3-methoxyphenyl)-2-hydroxyethyl]-3-(hydroxymethyl)piperazine-1-carboxylate

2-(methyloxy)-4-oxiran-2-ylbenzonitrile

vanillin triflate

4-formyl-2-methoxybenzonitrile

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