(R)-2,6-Dimethyl-heptanoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

Base Information

• Chemical Name: (R)-2,6-Dimethyl-heptanoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester
• CAS No.: 86534-80-7
• Molecular Formula: C₃₃H₄₇NO₄S
• Molecular Weight: 553.806
• Mol file: 86534-80-7.mol

Synonyms:

Chemical Property of (R)-2,6-Dimethyl-heptanoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2,6-Dimethyl-heptanoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

There total 2 articles about (R)-2,6-Dimethyl-heptanoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl 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:

1-iodo-4-methylpentane (6196-80-1) + Propionic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (76529-60-7) → (R)-2,6-Dimethyl-heptanoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (86534-80-7) + (S)-2,6-Dimethyl-heptanoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (86534-80-7)

Guidance literature:

With lithium cyclohexylisopropylamide; Yield given. Multistep reaction. Yields of byproduct given; 1) THF - HMPT, -80 deg C, 2) -80 to -40 deg C;

DOI:10.1016/S0040-4039(00)81623-8

Reference yield:

1-iodo-4-methylpentane (6196-80-1) + Propionic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (76529-60-7) → (R)-2,6-Dimethyl-heptanoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (86534-80-7) + (S)-2,6-Dimethyl-heptanoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (86534-80-7)

Guidance literature:

With lithium cyclohexylisopropylamide; Yield given. Multistep reaction. Yields of byproduct given; 1) THF - HMPT, -80 deg C, 2) -80 to -40 deg C;

DOI:10.1016/S0040-4039(00)81623-8

Reference yield:

(R)-2,6-Dimethyl-heptanoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (86534-80-7) → (2R,6R)-2,6,10-Trimethyl-undecanoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (86534-87-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / LAH / tetrahydrofuran

2: 93 percent / aq. HI (56percent) / Heating

3: 1) lithium cyclohexylisopropylamide, 2) TMEDA / 1) THF, -80 deg C 2) -80 to 0 deg C

4: 94 percent / H₂O / n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / Ambient temperature

5: 99 percent / LiAlH₄ / tetrahydrofuran

6: aq. HI (56percent) / Heating

7: 1) lithium cyclohexylisopropylamide, 2) N,N-dimethylimidazolidinone / 1) THF, -80 deg C, 2) -80 to -40 deg C

With 1,3-dimethyl-2-imidazolidinone; lithium aluminium tetrahydride; N,N,N,N,-tetramethylethylenediamine; water; hydrogen iodide; lithium cyclohexylisopropylamide; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)81623-8

upstream raw materials:

1-iodo-4-methylpentane

Propionic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

Downstream raw materials:

(2R,6R)-2,6,10-Trimethyl-undecanoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester