(3S,5aR,6aS,7aS)-3-(4-methoxybenzyl)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one

Base Information

• Chemical Name: (3S,5aR,6aS,7aS)-3-(4-methoxybenzyl)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one
• CAS No.: 1266680-99-2
• Molecular Formula: C₂₁H₂₇NO₃
• Molecular Weight: 341.45

Synonyms:(3S,5aR,6aS,7aS)-3-(4-methoxybenzyl)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one

Chemical Property of (3S,5aR,6aS,7aS)-3-(4-methoxybenzyl)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one

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Technology Process of (3S,5aR,6aS,7aS)-3-(4-methoxybenzyl)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one

There total 4 articles about (3S,5aR,6aS,7aS)-3-(4-methoxybenzyl)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one 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: 89.0%

(5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-2(3H)-one (1266680-97-0) + p-methoxybenzyl chloride (824-94-2) → (3S,5aR,6aS,7aS)-3-(4-methoxybenzyl)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-2(3H)-one (1266680-99-2)

Guidance literature:

With tetrabutylammomium bromide; potassium hydroxide; In water; toluene; at 20 ℃; for 0.333333h; optical yield given as %de; diastereoselective reaction;

DOI:10.1021/jo1022537

Reference yield: 88.0%

(5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-2(3H)-one (1266680-97-0) + p-Methoxybenzyl bromide (2746-25-0) → (3S,5aR,6aS,7aS)-3-(4-methoxybenzyl)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-2(3H)-one (1266680-99-2)

Guidance literature:

With tetrabutylammomium bromide; potassium hydroxide; In water; toluene; at 20 ℃; for 0.333333h; optical yield given as %de; diastereoselective reaction;

DOI:10.1021/jo1022537

Reference yield:

C21H27NO5 → (3S,5aR,6aS,7aS)-3-(4-methoxybenzyl)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-2(3H)-one (1266680-99-2)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 17 h / 20 °C

2: tetrabutylammomium bromide; potassium hydroxide / water; toluene / 0.33 h / 20 °C

With palladium 10% on activated carbon; tetrabutylammomium bromide; hydrogen; potassium hydroxide; In methanol; water; toluene;

DOI:10.1021/jo1022537

upstream raw materials:

(5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one

p-Methoxybenzyl bromide

p-methoxybenzyl chloride

(+)-Δ³-carene

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