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

Base Information

• Chemical Name: (+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1S,3R)-1-amino-3-hydroxy-1-cyclohexanecarboxylate
• CAS No.: 176965-97-2
• Molecular Formula: C₂₃H₃₅NO₃
• Molecular Weight: 373.536
• Mol file: 176965-97-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1S,3R)-1-amino-3-hydroxy-1-cyclohexanecarboxylate 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: 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

Reference yield:

(+)-(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 (1S,3R)-1-amino-3-hydroxy-1-cyclohexanecarboxylate (176965-97-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / Bu₃SnH / CH₂Cl₂ / 6 h / 40 °C

2: 95 percent / aq. TFA / tetrahydrofuran / 36 h / 80 °C

With tri-n-butyl-tin hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

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 (1S,3R)-1-amino-3-hydroxy-1-cyclohexanecarboxylate (176965-97-2)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 95 percent / aq. TFA / tetrahydrofuran / 36 h / 80 °C

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

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

upstream raw materials:

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

(+)-(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:

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