(1S,2R,5S,8R)-5-Benzyl-8,11,11-trimethyl-3-oxa-6-aza-tricyclo[6.2.1.0^2,7]undec-6-en-4-one

Base Information

• Chemical Name: (1S,2R,5S,8R)-5-Benzyl-8,11,11-trimethyl-3-oxa-6-aza-tricyclo[6.2.1.0^2,7]undec-6-en-4-one
• CAS No.: 500137-58-6
• Molecular Formula: C₁₉H₂₃NO₂
• Molecular Weight: 297.397

Synonyms:(1S,2R,5S,8R)-5-Benzyl-8,11,11-trimethyl-3-oxa-6-aza-tricyclo[6.2.1.0^2,7]undec-6-en-4-one

Chemical Property of (1S,2R,5S,8R)-5-Benzyl-8,11,11-trimethyl-3-oxa-6-aza-tricyclo[6.2.1.0^2,7]undec-6-en-4-one

Chemical Property:

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Technology Process of (1S,2R,5S,8R)-5-Benzyl-8,11,11-trimethyl-3-oxa-6-aza-tricyclo[6.2.1.0^2,7]undec-6-en-4-one

There total 11 articles about (1S,2R,5S,8R)-5-Benzyl-8,11,11-trimethyl-3-oxa-6-aza-tricyclo[6.2.1.0^2,7]undec-6-en-4-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: 88.0%

benzyl bromide (100-39-0) + (1S,2R,8R)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]-undec-6-en-4-one (500137-55-3) → (1S,2R,5S,8R)-5-Benzyl-8,11,11-trimethyl-3-oxa-6-aza-tricyclo[6.2.1.02,7]undec-6-en-4-one (500137-58-6)

Guidance literature:

(1S,2R,8R)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]-undec-6-en-4-one; With lithium diisopropyl amide; In tetrahydrofuran; at -30 ℃; for 1.5h;

benzyl bromide; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at -78 ℃; for 14h;

DOI:10.1021/jo026285a

Reference yield: 85.0%

benzyl chloride (100-44-7) + (1S,2R,8R)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]-undec-6-en-4-one (500137-55-3) → (1S,2R,5S,8R)-5-Benzyl-8,11,11-trimethyl-3-oxa-6-aza-tricyclo[6.2.1.02,7]undec-6-en-4-one (500137-58-6)

Guidance literature:

(1S,2R,8R)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]-undec-6-en-4-one; With lithium diisopropyl amide; In tetrahydrofuran; at -45 ℃; for 0.166667h;

benzyl chloride; In tetrahydrofuran; at -78 - -40 ℃; stereoselective reaction;

DOI:10.1021/acs.orglett.7b02296

Reference yield:

(R)-camphorquinone (10334-26-6) → (1S,2R,5S,8R)-5-Benzyl-8,11,11-trimethyl-3-oxa-6-aza-tricyclo[6.2.1.02,7]undec-6-en-4-one (500137-58-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium borohydride / diethyl ether; methanol / 0.5 h / cooling

1.2: 4-(N,N-dimethylamino)pyridine; dicyclohexylcarbodiimide / tetrahydrofuran / 18 h / 0 - 20 °C

1.3: 1.24 g / H₂ / Pd/C / ethanol / 14 h / 25 °C / 760 Torr

2.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 1.5 h / -30 °C

2.2: hexamethylphosphoric triamide / tetrahydrofuran; hexane / -78 °C

2.3: tetrahydrofuran; hexane / 12 h / -78 °C

With sodium tetrahydroborate; n-butyllithium; diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; hexane;

DOI:10.1021/jo052435g

upstream raw materials:

benzyl bromide

(1S,2R,8R)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]-undec-6-en-4-one

(R)-camphorquinone

(+)-3R-exo-hydroxycamphor

Downstream raw materials:

L-phenylalanine

(1S,2R,5R,8R)-5-allyl-5-benzyl-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one

(1S,2R,5R,8R)-5-benzyl-5,8,11,11-tetramethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one

(R)-2-amino-2-methyl-3-phenylpropanoic acid

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