(2R,3S,4S)-3-Ethoxycarbonylmethyl-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester

Base Information

• Chemical Name: (2R,3S,4S)-3-Ethoxycarbonylmethyl-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester
• CAS No.: 206126-48-9
• Molecular Formula: C₂₂H₂₉NO₆
• Molecular Weight: 403.475

Synonyms:(2R,3S,4S)-3-Ethoxycarbonylmethyl-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester

Chemical Property of (2R,3S,4S)-3-Ethoxycarbonylmethyl-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-3-Ethoxycarbonylmethyl-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester

There total 14 articles about (2R,3S,4S)-3-Ethoxycarbonylmethyl-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-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: 50.0%

(2R,3S,4R)-4-[1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-ethoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester (206126-47-8) → (2R,3S,4S)-3-Ethoxycarbonylmethyl-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester (206126-48-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(98)00166-X

Reference yield:

(S)-ethyl N-tert-butoxycarbonylpyroglutamate (144978-35-8,144978-12-1,251924-83-1) → (2R,3S,4S)-3-Ethoxycarbonylmethyl-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester (206126-48-9)

Guidance literature:

Multi-step reaction with 14 steps

1: LiHMDS, Et₂OBF₃

2: TFA / CH₂Cl₂

3: DMAP

4: 2,6-lutidine

5: 66 percent / 1.) DIBAL-H; 2.) Et₃SiH, Et₂O*BF₃

6: 1.) LiHMDS; 2.) PhSeCl / 1.) THF, 0 deg C; 2.) r.t.

7: 65 percent / NaH / tetrahydrofuran

8: KHMDS / tetrahydrofuran / 0 - 20 °C

9: hydrogen peroxide / tetrahydrofuran / 0 °C

10: 78 percent / hydrogen / PtO₂ / ethanol / 360 h / 4137.2 Torr

11: 67 percent / aq. NaCl / dimethylsulfoxide / 2 h / 170 °C

12: TFA

13: Et₃N

14: 50 percent / EtO₂*BF₃ / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; triethylsilane; dmap; Phenylselenyl chloride; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; triethylamine; trifluoroacetic acid; sodium chloride; lithium hexamethyldisilazane; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(98)00166-X

Reference yield:

(S)-4-(1-Hydroxy-1-methyl-ethyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (1066877-98-2) → (2R,3S,4S)-3-Ethoxycarbonylmethyl-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester (206126-48-9)

Guidance literature:

Multi-step reaction with 13 steps

1: TFA / CH₂Cl₂

2: DMAP

3: 2,6-lutidine

4: 66 percent / 1.) DIBAL-H; 2.) Et₃SiH, Et₂O*BF₃

5: 1.) LiHMDS; 2.) PhSeCl / 1.) THF, 0 deg C; 2.) r.t.

6: 65 percent / NaH / tetrahydrofuran

7: KHMDS / tetrahydrofuran / 0 - 20 °C

8: hydrogen peroxide / tetrahydrofuran / 0 °C

9: 78 percent / hydrogen / PtO₂ / ethanol / 360 h / 4137.2 Torr

10: 67 percent / aq. NaCl / dimethylsulfoxide / 2 h / 170 °C

11: TFA

12: Et₃N

13: 50 percent / EtO₂*BF₃ / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; triethylsilane; dmap; Phenylselenyl chloride; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; triethylamine; trifluoroacetic acid; sodium chloride; lithium hexamethyldisilazane; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(98)00166-X

upstream raw materials:

(2R,3S,4R)-4-[1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-ethoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

(S)-4-(1-Hydroxy-1-methyl-ethyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

(2S,4R)-4-[1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Downstream raw materials:

(2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester

(-)-kainic acid

1-(benzyloxycarbonyl)kainic acid dimethyl ester

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