Phenyl-acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Base Information

• Chemical Name: Phenyl-acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
• CAS No.: 104897-86-1
• Molecular Formula: C₃₀H₄₅NO₄S
• Molecular Weight: 515.758
• Mol file: 104897-86-1.mol

Synonyms:Phenyl-acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Chemical Property of Phenyl-acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phenyl-acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

There total 11 articles about Phenyl-acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-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:

(-)-10-dicyclohexylsulfamoyl-D-isoborneol (96303-88-7) → Phenyl-acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (104897-86-1)

Guidance literature:

Multi-step reaction with 9 steps

1: AgCN

2: 1.) n-BuLi, diisopropylamine / 1.) THF, hexane, - 78 deg C 2.) -78 deg C, 1 h.

3: 66 percent / N-Bromo-succinimide / 1,2-dimethoxy-ethane / 0.5 h / -78 °C / d.e. 96percent

4: 90 percent / Ca(BH₄)2 / tetrahydrofuran

5: AgCN

6: 1.) n-BuLi, diisopropylamine / 1.) THF, hexane, - 78 deg C 2.) -78 deg C, 1 h.

7: 67 percent / N-Chloro-succinimide / tetrahydrofuran / 1.) -78 deg C, 3 h 2.) 0 deg C, 30 min. d.e. 96 percent

8: 90 percent / Ca(BH₄)2 / tetrahydrofuran

9: AgCN

With N-chloro-succinimide; N-Bromosuccinimide; n-butyllithium; calcium borohydride; silver cyanide; diisopropylamine; In tetrahydrofuran; 1,2-dimethoxyethane;

Reference yield:

(S)-2-Chloro-propionic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (104897-94-1) → Phenyl-acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (104897-86-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / Ca(BH₄)2 / tetrahydrofuran

2: AgCN

3: 1.) n-BuLi, diisopropylamine / 1.) THF, hexane, - 78 deg C 2.) -78 deg C, 1 h.

4: 66 percent / N-Bromo-succinimide / 1,2-dimethoxy-ethane / 0.5 h / -78 °C / d.e. 96percent

5: 90 percent / Ca(BH₄)2 / tetrahydrofuran

6: AgCN

7: 1.) n-BuLi, diisopropylamine / 1.) THF, hexane, - 78 deg C 2.) -78 deg C, 1 h.

8: 67 percent / N-Chloro-succinimide / tetrahydrofuran / 1.) -78 deg C, 3 h 2.) 0 deg C, 30 min. d.e. 96 percent

9: 90 percent / Ca(BH₄)2 / tetrahydrofuran

10: AgCN

With N-chloro-succinimide; N-Bromosuccinimide; n-butyllithium; calcium borohydride; silver cyanide; diisopropylamine; In tetrahydrofuran; 1,2-dimethoxyethane;

Reference yield:

N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((E)-1-trimethylsilanyloxy-propenyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide (104897-88-3) → Phenyl-acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (104897-86-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 77 percent / N-Chloro-succinimide / tetrahydrofuran / 1.) -78 to 0 deg C, 3 h 2.) 0 deg C, 30 min., d.e. = 98 percent

2: 90 percent / Ca(BH₄)2 / tetrahydrofuran

3: AgCN

4: 1.) n-BuLi, diisopropylamine / 1.) THF, hexane, - 78 deg C 2.) -78 deg C, 1 h.

5: 66 percent / N-Bromo-succinimide / 1,2-dimethoxy-ethane / 0.5 h / -78 °C / d.e. 96percent

6: 90 percent / Ca(BH₄)2 / tetrahydrofuran

7: AgCN

8: 1.) n-BuLi, diisopropylamine / 1.) THF, hexane, - 78 deg C 2.) -78 deg C, 1 h.

9: 67 percent / N-Chloro-succinimide / tetrahydrofuran / 1.) -78 deg C, 3 h 2.) 0 deg C, 30 min. d.e. 96 percent

10: 90 percent / Ca(BH₄)2 / tetrahydrofuran

11: AgCN

With N-chloro-succinimide; N-Bromosuccinimide; n-butyllithium; calcium borohydride; silver cyanide; diisopropylamine; In tetrahydrofuran; 1,2-dimethoxyethane;

upstream raw materials:

(-)-10-dicyclohexylsulfamoyl-D-isoborneol

phenylacetyl chloride

<(2S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> 4-methylvalerate

N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((E)-1-trimethylsilanyloxy-propenyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide

Downstream raw materials:

N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((Z)-2-phenyl-1-trimethylsilanyloxy-vinyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide

(R)-Styrene oxide

(S)-styrene oxide

(-)-10-dicyclohexylsulfamoyl-D-isoborneol