(1R,2S,3R,4S)-2-Benzoylamino-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-methyl ester

Base Information

• Chemical Name: (1R,2S,3R,4S)-2-Benzoylamino-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-methyl ester
• CAS No.: 178232-11-6
• Molecular Formula: C₁₇H₁₉NO₅
• Molecular Weight: 317.342
• Mol file: 178232-11-6.mol

Synonyms:(1R,2S,3R,4S)-2-Benzoylamino-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-methyl ester

Chemical Property of (1R,2S,3R,4S)-2-Benzoylamino-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3R,4S)-2-Benzoylamino-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-methyl ester

There total 4 articles about (1R,2S,3R,4S)-2-Benzoylamino-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-methyl 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: 87.0%

methyl (1R,2S,3R,4S)-2-benzamido-3-(1,2-dihydroxyethyl)bicyclo[2.2.1]heptane-2-carboxylate (178232-10-5) → (1R,2S,3R,4S)-2-Benzoylamino-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-methyl ester (178232-11-6)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; acetonitrile; for 24h; Ambient temperature;

DOI:10.1016/0957-4166(96)00172-3

Reference yield:

(1S,2S,3R,4R)-3-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-bicyclo<2.2.1>-hept-5-en-2-spiro<4'<2'-phenyl-5'(4'H)-oxazolone>> (156038-73-2) → (1R,2S,3R,4S)-2-Benzoylamino-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-methyl ester (178232-11-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / MeONa / 0.5 h / Ambient temperature

2: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 4 h / 760 Torr

3: 96 percent / 3N aq. HCl / methanol / 24 h / Ambient temperature

4: 87 percent / aq. NaIO₄, RuCl₃*H₂O / acetonitrile; CCl₄ / 24 h / Ambient temperature

With hydrogenchloride; ruthenium trichloride; sodium periodate; hydrogen; sodium methylate; palladium on activated charcoal; In methanol; tetrachloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/0957-4166(96)00172-3

Reference yield:

(1S,2S,3R,4R)-2-Benzoylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (178232-08-1) → (1R,2S,3R,4S)-2-Benzoylamino-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-methyl ester (178232-11-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 4 h / 760 Torr

2: 96 percent / 3N aq. HCl / methanol / 24 h / Ambient temperature

3: 87 percent / aq. NaIO₄, RuCl₃*H₂O / acetonitrile; CCl₄ / 24 h / Ambient temperature

With hydrogenchloride; ruthenium trichloride; sodium periodate; hydrogen; palladium on activated charcoal; In methanol; tetrachloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/0957-4166(96)00172-3

upstream raw materials:

methyl (1R,2S,3R,4S)-2-benzamido-3-(1,2-dihydroxyethyl)bicyclo[2.2.1]heptane-2-carboxylate

(1S,2S,3R,4R)-3-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-bicyclo<2.2.1>-hept-5-en-2-spiro<4'<2'-phenyl-5'(4'H)-oxazolone>>

(1R,2S,3R,4S)-2-Benzoylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

(1S,2S,3R,4R)-2-Benzoylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester