(1S,2S,1'S)-N-2''-chloroacetyl-2-(1'-phenyl)-ethyl-aminocyclohexanol

Base Information

• Chemical Name: (1S,2S,1'S)-N-2''-chloroacetyl-2-(1'-phenyl)-ethyl-aminocyclohexanol
• CAS No.: 777939-67-0
• Molecular Formula: C₁₆H₂₂ClNO₂
• Molecular Weight: 295.809
• Mol file: 777939-67-0.mol

Synonyms:(1S,2S,1'S)-N-2''-chloroacetyl-2-(1'-phenyl)-ethyl-aminocyclohexanol

Chemical Property of (1S,2S,1'S)-N-2''-chloroacetyl-2-(1'-phenyl)-ethyl-aminocyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,1'S)-N-2''-chloroacetyl-2-(1'-phenyl)-ethyl-aminocyclohexanol

There total 1 articles about (1S,2S,1'S)-N-2''-chloroacetyl-2-(1'-phenyl)-ethyl-aminocyclohexanol 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: 24.0%

trans-(1'S)2-N-[(α-phenylethyl)amino]cyclohexanol (666845-36-9) + chloroacetyl chloride (79-04-9) → 2-chloro-N-(2-hydroxy-cyclohexyl)-N-(1-phenyl-ethyl)-acetamide + (1S,2S,1'S)-N-2''-chloroacetyl-2-(1'-phenyl)-ethyl-aminocyclohexanol (777939-67-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/ol048861q

Reference yield: 92.0%

(1S,2S,1'S)-N-2''-chloroacetyl-2-(1'-phenyl)-ethyl-aminocyclohexanol (777939-67-0) → (4aS,8aS,1'S)-N-(1'-phenyl)-ethyl-4-oxa-perhydrochinolin-2-on (777939-68-1)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.75h;

DOI:10.1021/ol048861q

Reference yield:

(1S,2S,1'S)-N-2''-chloroacetyl-2-(1'-phenyl)-ethyl-aminocyclohexanol (777939-67-0) → C31H45N3O6

Guidance literature:

Multi-step reaction with 7 steps

1.1: 92 percent / KOtBu / tetrahydrofuran / 0.75 h / 0 °C

2.1: 60 percent / formic acid / 8 h / 100 °C

3.1: 77 percent / nBuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

4.1: 31 percent / HMDS; nBuLi / tetrahydrofuran; hexane / 18 h / -78 - 0 °C

5.1: 67 percent / LiOH; H₂O₂ / H₂O; tetrahydrofuran / 1.5 h / -18 - 0 °C

6.1: H₂ / 5 percent Pd/C / methanol

6.2: 77 percent / HOBt; NEt₃; EDC / CH₂Cl₂ / 20 °C

7.1: TFA / CH₂Cl₂ / 1.5 h / 20 °C

7.2: H₂ / 5 percent Pd/C / methanol

7.3: 86 percent / HATU; HOAt; DIEA / CH₂Cl₂ / 12 h / 20 °C

With lithium hydroxide; n-butyllithium; potassium tert-butylate; hydrogen; dihydrogen peroxide; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; formic acid; hexane; dichloromethane; water;

DOI:10.1021/ol048861q

upstream raw materials:

trans-(1'S)2-N-[(α-phenylethyl)amino]cyclohexanol

chloroacetyl chloride

Downstream raw materials:

(4aS,8aS,1'S)-N-(1'-phenyl)-ethyl-4-oxa-perhydrochinolin-2-on

(4aS,8aS)-N-carboxybenzyl-4-oxa-perhydrochinolin-2-on

(3R,4aS,8aS)-N-carboxybenzyl-3-benzyl-4-oxa-perhydrochinolin-2-on

(2R,1'S,2'S)-2-(2'-carboxybenzylamino-cyclohexyl)oxy-3-phenyl-propionic acid