2-(S-1-phenylethylamino)-cyclohex-1-enecarboxylic acid ethyl ester

Base Information

• Chemical Name: 2-(S-1-phenylethylamino)-cyclohex-1-enecarboxylic acid ethyl ester
• CAS No.: 53898-03-6
• Molecular Formula: C₁₇H₂₃NO₂
• Molecular Weight: 273.375
• Mol file: 53898-03-6.mol

Synonyms:2-(S-1-phenylethylamino)-cyclohex-1-enecarboxylic acid ethyl ester

Chemical Property of 2-(S-1-phenylethylamino)-cyclohex-1-enecarboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(S-1-phenylethylamino)-cyclohex-1-enecarboxylic acid ethyl ester

There total 1 articles about 2-(S-1-phenylethylamino)-cyclohex-1-enecarboxylic acid ethyl 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: 77.0%

(S)-1-phenyl-ethylamine (2627-86-3) + ethyl 2-oxocyclohexane carboxylate (1655-07-8) → 2-(S-1-phenylethylamino)-cyclohex-1-enecarboxylic acid ethyl ester (53898-03-6)

Guidance literature:

In toluene; Heating;

DOI:10.1016/S0957-4166(00)82164-3

Reference yield:

2-(S-1-phenylethylamino)-cyclohex-1-enecarboxylic acid ethyl ester (53898-03-6) → phenylmethyl-(2S,3aR,7aS)-octahydroindole-2-carboxylate hydrochloride (145641-35-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium tetrahydroborate; acetic acid / acetonitrile / 2 - 22 °C / Inert atmosphere

1.2: pH ~ 8

2.1: sodium t-butanolate / tert-butyl alcohol; tetrahydrofuran / 5 h / 6 - 22 °C / Inert atmosphere

3.1: lithium borohydride / tetrahydrofuran / 12 h / 15 °C / Reflux; Inert atmosphere

3.2: 0.5 h / 5 - 15 °C

3.3: pH ~ 8.7

4.1: sodium carbonate / acetonitrile / 18 h / Reflux; Inert atmosphere

5.1: triethylamine / dichloromethane / 1.42 h / 2 - 22 °C / Inert atmosphere

6.1: sodium t-butanolate / tetrahydrofuran / 1 h / 19 - 65 °C / Inert atmosphere

7.1: hydrogen / 5% Pd(II)/C(eggshell) / ethanol / 3 h / 60 °C / 749.88 Torr

8.1: hydrogenchloride; water / 4 h / Reflux

9.1: thionyl chloride / dichloromethane

With hydrogenchloride; sodium tetrahydroborate; lithium borohydride; thionyl chloride; water; hydrogen; sodium carbonate; acetic acid; triethylamine; sodium t-butanolate; 5% Pd(II)/C(eggshell); In tetrahydrofuran; ethanol; dichloromethane; acetonitrile; tert-butyl alcohol;

Reference yield:

2-(S-1-phenylethylamino)-cyclohex-1-enecarboxylic acid ethyl ester (53898-03-6) → (2S,3aR,7aS)-octahydro-1H-indole-2-carboxylic acid hydrochloride (144540-75-0,1004292-98-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium tetrahydroborate; acetic acid / acetonitrile / 2 - 22 °C / Inert atmosphere

1.2: pH ~ 8

2.1: sodium t-butanolate / tert-butyl alcohol; tetrahydrofuran / 5 h / 6 - 22 °C / Inert atmosphere

3.1: lithium borohydride / tetrahydrofuran / 12 h / 15 °C / Reflux; Inert atmosphere

3.2: 0.5 h / 5 - 15 °C

3.3: pH ~ 8.7

4.1: sodium carbonate / acetonitrile / 18 h / Reflux; Inert atmosphere

5.1: triethylamine / dichloromethane / 1.42 h / 2 - 22 °C / Inert atmosphere

6.1: sodium t-butanolate / tetrahydrofuran / 1 h / 19 - 65 °C / Inert atmosphere

7.1: hydrogen / 5% Pd(II)/C(eggshell) / ethanol / 3 h / 60 °C / 749.88 Torr

8.1: hydrogenchloride; water / 4 h / Reflux

With hydrogenchloride; sodium tetrahydroborate; lithium borohydride; water; hydrogen; sodium carbonate; acetic acid; triethylamine; sodium t-butanolate; 5% Pd(II)/C(eggshell); In tetrahydrofuran; ethanol; dichloromethane; acetonitrile; tert-butyl alcohol;

upstream raw materials:

(S)-1-phenyl-ethylamine

ethyl 2-oxocyclohexane carboxylate

Downstream raw materials:

(S)-1-(2-tert-Butoxycarbonyl-ethyl)-2-oxo-cyclohexanecarboxylic acid ethyl ester

(R)-1-(2-tert-Butoxycarbonyl-ethyl)-2-oxo-cyclohexanecarboxylic acid ethyl ester

(+)-(R)-2-Oxo-1-(3-oxo-1-butyl)-cyclohexancarbonsaeureaethylester

(-)-(S)-2-Oxo-1-(3-oxo-1-butyl)-cyclohexancarbonsaeureaethylester

Refernces

• 1、 -. "PROCESSES FOR THE SYNTHESIS OF (2S, 3AR, 7AS)-OCTAHYDRO-1H-INDOLE CARBOXYLIC ACID AS AN INTERMEDIATE FOR TRANDOLAPRIL". Page/Page column 20. . Retrieved 2011/02/24.
• 2、 Xu, Daqiang,Prasad, Kapa,Repic, Oljan,Blacklock, Thomas J.. "A practical synthesis of enantiopure ethyl cis-2-amino-1-cyclohexanecarboxylate via asymmetric reductive amination methodology". . p. 1445 - 1451. Retrieved 2007/10/03.