(1R,2R,7R,10S)-4-Ethyl-3-oxo-6-oxa-13-aza-tricyclo[8.2.1.0^2,7]tridec-4-ene-13-carboxylic acid benzyl ester

Base Information

• Chemical Name: (1R,2R,7R,10S)-4-Ethyl-3-oxo-6-oxa-13-aza-tricyclo[8.2.1.0^2,7]tridec-4-ene-13-carboxylic acid benzyl ester
• CAS No.: 382141-49-3
• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.434

Synonyms:(1R,2R,7R,10S)-4-Ethyl-3-oxo-6-oxa-13-aza-tricyclo[8.2.1.0^2,7]tridec-4-ene-13-carboxylic acid benzyl ester

Chemical Property of (1R,2R,7R,10S)-4-Ethyl-3-oxo-6-oxa-13-aza-tricyclo[8.2.1.0^2,7]tridec-4-ene-13-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,7R,10S)-4-Ethyl-3-oxo-6-oxa-13-aza-tricyclo[8.2.1.0^2,7]tridec-4-ene-13-carboxylic acid benzyl ester

There total 16 articles about (1R,2R,7R,10S)-4-Ethyl-3-oxo-6-oxa-13-aza-tricyclo[8.2.1.0^2,7]tridec-4-ene-13-carboxylic acid benzyl 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: 91.0%

(1R,2S,3R,6S)-2-{2-[(E)-tert-Butylimino-methyl]-butyryl}-3-hydroxy-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid benzyl ester (382141-48-2) → (1R,2R,7R,10S)-4-Ethyl-3-oxo-6-oxa-13-aza-tricyclo[8.2.1.02,7]tridec-4-ene-13-carboxylic acid benzyl ester (382141-49-3)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1016/S0040-4039(01)01583-0

Reference yield:

Cbz-L-pGlu-OH (32159-21-0) → (1R,2R,7R,10S)-4-Ethyl-3-oxo-6-oxa-13-aza-tricyclo[8.2.1.02,7]tridec-4-ene-13-carboxylic acid benzyl ester (382141-49-3)

Guidance literature:

Multi-step reaction with 16 steps

1.1: ClCOOEt; N-methylmorpholine / tetrahydrofuran / -10 °C

1.2: 61 percent / NaBH₄ / methanol / 0 °C

2.1: 92 percent / DIBAL-H / CH₂Cl₂ / -78 °C

3.1: 93 percent / p-TsOH / 20 °C

4.1: 90 percent / pyridine / 0 °C

5.1: 60 percent / NaI; CaCO₃ / dimethylformamide / 80 °C

6.1: SO₃-pyridine; Et₃N / dimethylsulfoxide / 20 °C

7.1: tetrahydrofuran / 20 °C

8.1: 100 percent / NaBH₄; CuCl / methanol; tetrahydrofuran / 0 °C

9.1: 84 percent / aq. NaOH / methanol / 20 °C

10.1: tetrahydrofuran / 20 °C

10.2: 62 percent / LDA / 0 °C

11.1: TBSCl; Et₃N / tetrahydrofuran / 40 °C

11.2: 78 percent / Sn(OTf)2 / CH₂Cl₂ / 0 °C

12.1: 90 percent / NaBH₄ / methanol / 0 °C

13.1: TFA / CH₂Cl₂ / 20 °C

14.1: methanol / 20 °C

15.1: 73 percent / LDA / tetrahydrofuran / 0 °C

16.1: 91 percent / TFA / tetrahydrofuran; H₂O / 20 °C

With 4-methyl-morpholine; pyridine; sodium hydroxide; sodium tetrahydroborate; pyridine-SO₃ complex; chloroformic acid ethyl ester; diisobutylaluminium hydride; toluene-4-sulfonic acid; tert-butyldimethylsilyl chloride; triethylamine; trifluoroacetic acid; calcium carbonate; sodium iodide; copper(l) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 7.1: Wittig reaction;

DOI:10.1016/S0040-4039(01)01583-0

Reference yield:

benzyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate (153870-19-0) → (1R,2R,7R,10S)-4-Ethyl-3-oxo-6-oxa-13-aza-tricyclo[8.2.1.02,7]tridec-4-ene-13-carboxylic acid benzyl ester (382141-49-3)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 92 percent / DIBAL-H / CH₂Cl₂ / -78 °C

2.1: 93 percent / p-TsOH / 20 °C

3.1: 90 percent / pyridine / 0 °C

4.1: 60 percent / NaI; CaCO₃ / dimethylformamide / 80 °C

5.1: SO₃-pyridine; Et₃N / dimethylsulfoxide / 20 °C

6.1: tetrahydrofuran / 20 °C

7.1: 100 percent / NaBH₄; CuCl / methanol; tetrahydrofuran / 0 °C

8.1: 84 percent / aq. NaOH / methanol / 20 °C

9.1: tetrahydrofuran / 20 °C

9.2: 62 percent / LDA / 0 °C

10.1: TBSCl; Et₃N / tetrahydrofuran / 40 °C

10.2: 78 percent / Sn(OTf)2 / CH₂Cl₂ / 0 °C

11.1: 90 percent / NaBH₄ / methanol / 0 °C

12.1: TFA / CH₂Cl₂ / 20 °C

13.1: methanol / 20 °C

14.1: 73 percent / LDA / tetrahydrofuran / 0 °C

15.1: 91 percent / TFA / tetrahydrofuran; H₂O / 20 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; pyridine-SO₃ complex; diisobutylaluminium hydride; toluene-4-sulfonic acid; tert-butyldimethylsilyl chloride; triethylamine; trifluoroacetic acid; calcium carbonate; sodium iodide; copper(l) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 6.1: Wittig reaction;

DOI:10.1016/S0040-4039(01)01583-0

upstream raw materials:

(1R,2S,3R,6S)-2-{2-[(E)-tert-Butylimino-methyl]-butyryl}-3-hydroxy-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid benzyl ester

Cbz-L-pGlu-OH

benzyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate

(S)-2-Formyl-5-methoxy-pyrrolidine-1-carboxylic acid benzyl ester

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