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

Base Information

• Chemical Name: (S)-1-Acetylamino-cyclohex-3-enecarboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
• CAS No.: 176965-94-9
• Molecular Formula: C₂₅H₃₅NO₃
• Molecular Weight: 397.558
• Mol file: 176965-94-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (S)-1-Acetylamino-cyclohex-3-enecarboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 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: 80.0%

(1R,2S,5R)-8-phenylmenthyl 2-acetamidoacrylate (145644-82-2) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → (S)-1-Acetylamino-cyclohex-3-enecarboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (176965-94-9)

Guidance literature:

With titanium tetrachloride; In dichloromethane; for 6h; Ambient temperature;

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

Reference yield: 100.0%

(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,5S,8S)-3-methyl-exo-8-iodo-2-oxa-4-azabicyclo<3.3.1>non-3-ene-5-carboxylate (176965-95-0)

Guidance literature:

With N-iodo-succinimide; In dichloromethane; for 14h; Ambient temperature;

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) → (+)-(1S,3R)-1-amino-3-hydroxy-1-cyclohexanecarboxylic acid (172299-73-9,177186-21-9)

Guidance literature:

Multi-step reaction with 4 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

4: 75 percent / 1.) 6 N aq. HCl, 2.) propylene oxide / ethanol / 1.) reflux, 24 h, 2.) reflux, 2 h

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

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

upstream raw materials:

(1R,2S,5R)-8-phenylmenthyl 2-acetamidoacrylate

buta-1,3-diene

Downstream 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

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

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

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