2-(1-tert-butoxycarbonyl-2-methyl-propylamino)-cyclohex-1-enecarboxylic acid ethyl ester

Base Information

• Chemical Name: 2-(1-tert-butoxycarbonyl-2-methyl-propylamino)-cyclohex-1-enecarboxylic acid ethyl ester
• CAS No.: 104316-13-4
• Molecular Formula: C₁₈H₃₁NO₄
• Molecular Weight: 325.448
• Mol file: 104316-13-4.mol

Synonyms:2-(1-tert-butoxycarbonyl-2-methyl-propylamino)-cyclohex-1-enecarboxylic acid ethyl ester

Chemical Property of 2-(1-tert-butoxycarbonyl-2-methyl-propylamino)-cyclohex-1-enecarboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(1-tert-butoxycarbonyl-2-methyl-propylamino)-cyclohex-1-enecarboxylic acid ethyl ester

There total 1 articles about 2-(1-tert-butoxycarbonyl-2-methyl-propylamino)-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: 83.0%

tert-butyl L-valinate (13211-31-9) + ethyl 2-oxocyclohexane carboxylate (1655-07-8) → 2-(1-tert-butoxycarbonyl-2-methyl-propylamino)-cyclohex-1-enecarboxylic acid ethyl ester (104316-13-4)

Guidance literature:

With boron trifluoride diethyl etherate; In benzene; for 18h; Heating;

DOI:10.1021/ol051184v

Reference yield: 53.0%

2-(1-tert-butoxycarbonyl-2-methyl-propylamino)-cyclohex-1-enecarboxylic acid ethyl ester (104316-13-4) + methyl iodide (74-88-4) → (1R)-1-methyl-2-oxo-cyclohexanecarboxylic acid ethyl ester (172825-16-0)

Guidance literature:

2-(1-tert-butoxycarbonyl-2-methyl-propylamino)-cyclohex-1-enecarboxylic acid ethyl ester; With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In hexane; toluene; at -78 ℃; for 0.5h;

methyl iodide; In hexane; toluene; for 3h; cooling;

DOI:10.1021/ol051184v

Reference yield:

2-(1-tert-butoxycarbonyl-2-methyl-propylamino)-cyclohex-1-enecarboxylic acid ethyl ester (104316-13-4) → C19H23NO2S (862563-57-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: LDA; HMPA / toluene; hexane / 0.5 h / -78 °C

1.2: 53 percent / toluene; hexane / 3 h / cooling

2.1: P₂O₅ / CH₂Cl₂ / 48 h / 23 °C

3.1: DIBAL-H / toluene; hexane / 0.33 h / 0 °C

4.1: 0.188 g / IBX / dimethylsulfoxide / 4 h / 23 °C

5.1: 94 percent / mCPBA / CH₂Cl₂ / 1 h / 0 °C

6.1: Et₃N; molecular sieves 3 Angstroem / methanol / 12 h / 23 °C

7.1: 0.38 g / NaBH₄ / methanol / 0.5 h

8.1: 77 percent / Br₂; AcOH / H₂O; methanol / 2.5 h / 0 °C

9.1: 70 percent / toluene / 15 h / 120 °C

10.1: L-Selectride / tetrahydrofuran / 1 h / -78 °C

10.2: 72 percent / tetrahydrofuran / -78 - 23 °C

11.1: 84 percent / Et₃N; formic acid / PdCl₂(PPh₃)2 / dimethylformamide / 5 h / 60 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; formic acid; 3 A molecular sieve; bromine; phosphorus pentoxide; L-Selectride; diisobutylaluminium hydride; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol051184v

upstream raw materials:

tert-butyl L-valinate

ethyl 2-oxocyclohexane carboxylate

Downstream raw materials:

(S)-ethyl cyclohexanone-2-(2,2-dicarbo-t-butoxy-ethyl)-2-carboxylate

(R)-ethyl cyclohexanone-2-(2,2-dicarbo-t-butoxy-ethyl)-2-carboxylate

ethyl (R)-1-(prop-2-enyl)-2-oxocyclohexanecarboxylate

ethyl (S)-1-allyl-2-oxocyclohexane-1-carboxylate