(+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1R,5S)-3-methyl-2-oxa-4-azabicyclo<3.3.1>non-3-ene-5-carboxylate

Base Information

• Chemical Name: (+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1R,5S)-3-methyl-2-oxa-4-azabicyclo<3.3.1>non-3-ene-5-carboxylate
• CAS No.: 176965-96-1
• Molecular Formula: C₂₅H₃₅NO₃
• Molecular Weight: 397.558

Synonyms:(+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1R,5S)-3-methyl-2-oxa-4-azabicyclo<3.3.1>non-3-ene-5-carboxylate

Chemical Property of (+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1R,5S)-3-methyl-2-oxa-4-azabicyclo<3.3.1>non-3-ene-5-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of (+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1R,5S)-3-methyl-2-oxa-4-azabicyclo<3.3.1>non-3-ene-5-carboxylate

There total 2 articles about (+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1R,5S)-3-methyl-2-oxa-4-azabicyclo<3.3.1>non-3-ene-5-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: 92.0%

(+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1S,5S,8S)-3-methyl-exo-8-iodo-2-oxa-4-azabicyclo<3.3.1>non-3-ene-5-carboxylate (176965-95-0) → (+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1R,5S)-3-methyl-2-oxa-4-azabicyclo<3.3.1>non-3-ene-5-carboxylate (176965-96-1)

Guidance literature:

With tri-n-butyl-tin hydride; In dichloromethane; at 40 ℃; for 6h;

DOI:10.1016/0957-4166(96)00067-5

Reference yield:

(S)-1-Acetylamino-cyclohex-3-enecarboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (176965-94-9) → (+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1R,5S)-3-methyl-2-oxa-4-azabicyclo<3.3.1>non-3-ene-5-carboxylate (176965-96-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / N-iodosuccinimide / CH₂Cl₂ / 14 h / Ambient temperature

2: 92 percent / Bu₃SnH / CH₂Cl₂ / 6 h / 40 °C

With N-iodo-succinimide; tri-n-butyl-tin hydride; In dichloromethane;

DOI:10.1016/0957-4166(96)00067-5

Reference yield: 95.0%

(+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1R,5S)-3-methyl-2-oxa-4-azabicyclo<3.3.1>non-3-ene-5-carboxylate (176965-96-1) → (+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1S,3R)-1-amino-3-hydroxy-1-cyclohexanecarboxylate (176965-97-2)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; at 80 ℃; for 36h;

DOI:10.1016/0957-4166(96)00067-5

upstream raw materials:

(+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1S,5S,8S)-3-methyl-exo-8-iodo-2-oxa-4-azabicyclo<3.3.1>non-3-ene-5-carboxylate

(S)-1-Acetylamino-cyclohex-3-enecarboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Downstream raw materials:

(+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1S,3R)-1-amino-3-hydroxy-1-cyclohexanecarboxylate

(+)-(1S,3R)-1-amino-3-hydroxy-1-cyclohexanecarboxylic acid

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