3-Pyrrolidineaceticacid,2-carboxy-5-methyl-4-(1-methylethenyl)-,(2R,3R,4R,5R)-rel-(9CI)

Base Information

• Chemical Name: 3-Pyrrolidineaceticacid,2-carboxy-5-methyl-4-(1-methylethenyl)-,(2R,3R,4R,5R)-rel-(9CI)
• CAS No.: 792173-16-1
• Molecular Formula: C₁₁H₁₇NO₄
• Molecular Weight: 227.26
• Mol file: 792173-16-1.mol

Synonyms:3-Pyrrolidineaceticacid,2-carboxy-5-methyl-4-(1-methylethenyl)-,(2R,3R,4R,5R)-rel-(9CI)

Chemical Property of 3-Pyrrolidineaceticacid,2-carboxy-5-methyl-4-(1-methylethenyl)-,(2R,3R,4R,5R)-rel-(9CI)

Chemical Property:

• PSA: 86.63000
• LogP: 1.04330

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Pyrrolidineaceticacid,2-carboxy-5-methyl-4-(1-methylethenyl)-,(2R,3R,4R,5R)-rel-(9CI)

There total 10 articles about 3-Pyrrolidineaceticacid,2-carboxy-5-methyl-4-(1-methylethenyl)-,(2R,3R,4R,5R)-rel-(9CI) 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:

(2SR,3SR,4SR,5SR)-N-(tert-butoxycarbonyl)-2-carboxy-4-isopropenyl-5-methylpyrrolidine-3-acetic acid → (2SR,3SR,4RS,5RS)-2-carboxy-4-isopropenyl-5-methylpyrrolidine-3-acetic acid (792173-16-1)

Guidance literature:

With hydrogenchloride; methyloxirane; In ethyl acetate; for 8h; Yield given; Ambient temperature; 1.) EtOAc, room temperature, 8 h, 2.) MeOH, room temperature, overnight;

DOI:10.1021/jo982109j

Reference yield:

(1R,3aR,4S,6aR)-4-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-3-oxo-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-tert-butyl ester 1-ethyl ester → (2SR,3SR,4RS,5RS)-2-carboxy-4-isopropenyl-5-methylpyrrolidine-3-acetic acid (792173-16-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) DIBAL-H, 2.) PTSA / 1.) THF, -78 deg C, 30 min, 2.) room temperature, overnight

2: 92 percent / CuBr*Me₂S, BF₃*OEt₂ / diethyl ether / 1.) -78 deg C, 15 min, 2.) room temperature, 1 h

3: BF₃*OEt₂ / CHCl₃ / 24 h / 100 - 110 °C

4: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

5: 1.) NMO, OsO₄, 2.) NaIO₄ / 1.) Me₂CO, H₂O, room temperature, 24 h, 2.) THF, H₂O, room temperature, 5 h

6: Zn(BH₄)2 / tetrahydrofuran / 0.5 h / -10 °C

7: dioxane

8: Jones reagent / acetone / 1.) 0 deg C, 1 h, 2.) room temperature, 2 h

9: LiOH / tetrahydrofuran / 48 h / Ambient temperature

10: 1.) HCl, 2.) propylene oxide / ethyl acetate / 8 h / Ambient temperature; 1.) EtOAc, room temperature, 8 h, 2.) MeOH, room temperature, overnight

With hydrogenchloride; dmap; lithium hydroxide; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; jones reagent; zinc(II) tetrahydroborate; copper(I) bromide dimethylsulfide complex; boron trifluoride diethyl etherate; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; methyloxirane; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; chloroform; ethyl acetate; acetone;

DOI:10.1021/jo982109j

Reference yield:

ethyl (1SR,2SR,4SR,5SR)-3-aza-4,6-dimethylbicyclo<3.3.0>oct-6-ene-2-carboxylate → (2SR,3SR,4RS,5RS)-2-carboxy-4-isopropenyl-5-methylpyrrolidine-3-acetic acid (792173-16-1)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

2: 1.) NMO, OsO₄, 2.) NaIO₄ / 1.) Me₂CO, H₂O, room temperature, 24 h, 2.) THF, H₂O, room temperature, 5 h

3: Zn(BH₄)2 / tetrahydrofuran / 0.5 h / -10 °C

4: dioxane

5: Jones reagent / acetone / 1.) 0 deg C, 1 h, 2.) room temperature, 2 h

6: LiOH / tetrahydrofuran / 48 h / Ambient temperature

7: 1.) HCl, 2.) propylene oxide / ethyl acetate / 8 h / Ambient temperature; 1.) EtOAc, room temperature, 8 h, 2.) MeOH, room temperature, overnight

With hydrogenchloride; dmap; lithium hydroxide; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; jones reagent; zinc(II) tetrahydroborate; triethylamine; methyloxirane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; ethyl acetate; acetone;

DOI:10.1021/jo982109j

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