(1S,5R,6S)-N-(menthol-8-yl)-6-(o-methoxyphenyl)-3-azabicyclo[3.2.0]heptane

Base Information

• Chemical Name: (1S,5R,6S)-N-(menthol-8-yl)-6-(o-methoxyphenyl)-3-azabicyclo[3.2.0]heptane
• CAS No.: 565177-32-4
• Molecular Formula: C₂₃H₃₅NO₂
• Molecular Weight: 357.536

Synonyms:(1S,5R,6S)-N-(menthol-8-yl)-6-(o-methoxyphenyl)-3-azabicyclo[3.2.0]heptane

Chemical Property of (1S,5R,6S)-N-(menthol-8-yl)-6-(o-methoxyphenyl)-3-azabicyclo[3.2.0]heptane

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Technology Process of (1S,5R,6S)-N-(menthol-8-yl)-6-(o-methoxyphenyl)-3-azabicyclo[3.2.0]heptane

There total 2 articles about (1S,5R,6S)-N-(menthol-8-yl)-6-(o-methoxyphenyl)-3-azabicyclo[3.2.0]heptane 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: 96.0%

(2S,2aR,2bS,3aR,5R,7aS,10aS)-2-(2'-methoxyphenyl)-5,8,8-trimethylperhydrocyclobuta[3,4]pyrrolo[2,1-b]-[1,3]benzoxazin-10-one (565177-12-0) → (1S,5R,6S)-N-(menthol-8-yl)-6-(o-methoxyphenyl)-3-azabicyclo[3.2.0]heptane (565177-32-4)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In tetrahydrofuran; at -10 ℃; for 0.166667h;

DOI:10.1021/jo034251c

Reference yield:

N-acryloyl-2α-[2-trans-(2'-methoxyphenyl)ethenyl]-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine (402858-29-1) → (1S,5R,6S)-N-(menthol-8-yl)-6-(o-methoxyphenyl)-3-azabicyclo[3.2.0]heptane (565177-32-4)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 15 h / Irradiation

2: 96 percent / LiAlH₄; AlCl₃ / tetrahydrofuran / 0.17 h / -10 °C

With lithium aluminium tetrahydride; aluminium trichloride; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo034251c

Reference yield:

(1S,5R,6S)-N-(menthol-8-yl)-6-(o-methoxyphenyl)-3-azabicyclo[3.2.0]heptane (565177-32-4) → (2S,5R)-2-{1-[(1S,5R,6S)-6-(2-Methoxy-phenyl)-3-aza-bicyclo[3.2.0]hept-3-yl]-1-methyl-ethyl}-5-methyl-cyclohexanone

Guidance literature:

With 3 A molecular sieve; pyridinium chlorochromate; In dichloromethane; at 20 ℃;

DOI:10.1021/jo034251c

upstream raw materials:

(2S,2aR,2bS,3aR,5R,7aS,10aS)-2-(2'-methoxyphenyl)-5,8,8-trimethylperhydrocyclobuta[3,4]pyrrolo[2,1-b]-[1,3]benzoxazin-10-one

N-acryloyl-2α-[2-trans-(2'-methoxyphenyl)ethenyl]-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine

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