2-TERT-BUTOXYCARBONYLAMINO-3-OXO-OCTAHYDRO-INDOLIZINE-5-CARBOXYLIC ACID METHYL ESTER

Base Information

• Chemical Name: 2-TERT-BUTOXYCARBONYLAMINO-3-OXO-OCTAHYDRO-INDOLIZINE-5-CARBOXYLIC ACID METHYL ESTER
• CAS No.: 524958-63-2
• Molecular Formula: C₁₅H₂₄N₂O₅
• Molecular Weight: 312.366
• Mol file: 524958-63-2.mol

Synonyms:

Chemical Property of 2-TERT-BUTOXYCARBONYLAMINO-3-OXO-OCTAHYDRO-INDOLIZINE-5-CARBOXYLIC ACID METHYL ESTER

Chemical Property:

• Boiling Point: 460.5±34.0 °C(Predicted)
• PKA: 11.35±0.40(Predicted)
• Density: 1.21±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-TERT-BUTOXYCARBONYLAMINO-3-OXO-OCTAHYDRO-INDOLIZINE-5-CARBOXYLIC ACID METHYL ESTER

There total 25 articles about 2-TERT-BUTOXYCARBONYLAMINO-3-OXO-OCTAHYDRO-INDOLIZINE-5-CARBOXYLIC ACID 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:

(R)-5-heptene-1,2-diol (204120-73-0) → (2S,6S,8S)-methyl-8-[N-(tert-butoxycarbonyl)amino]-9-oxo-1-azabicyclo[4.3.0]nonane-2-carboxylate (524958-63-2)

Guidance literature:

Multi-step reaction with 19 steps

1.1: pyridinium p-toluenesulfonate; trimethyl orthoacetate / CH₂Cl₂ / 1 h / 20 °C

1.2: triethylamine; acetyl bromide / CH₂Cl₂ / 0.75 h

1.3: NaOH / diethyl ether; methanol / 2.5 h

2.1: (DHQD)2*PYR; K₃Fe(CN)6; aq. K₂CO₃ / K₂OsO₄*2H₂O / 2-methyl-propan-2-ol; H₂O / 14 h / 20 °C

3.1: molecular sieves 5 Angstroem; PPTS / CH₂Cl₂ / 20 h / 20 °C

4.1: coprous bromide; dimethyl sulfide / tetrahydrofuran / 1.5 h / -78 - 30 °C

5.1: aq. HCl / tetrahydrofuran / 2 h / 20 °C

6.1: imidazole / dimethylformamide / 5 h / 20 °C

7.1: triethylamine; 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 48 h / 20 °C

8.1: 48 h / 70 °C

9.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 20 °C

9.2: 81 percent / aq. NaOH; H₂O₂ / 1 h / 20 °C

10.1: hydrogen; Pd(OH)2 / methanol / 1 h

11.1: 675 mg / aq. K₂CO₃ / tetrahydrofuran / 5 h / 20 °C

12.1: aq. NaIO₄ / ruthenium(III) chloride hydrate / CCl₄; acetonitrile / 3 h

13.1: trifluoroacetic acid / CH₂Cl₂ / 1 h

13.2: 337 mg / 2,2'-dipyridinyl disulfide; triphenylphosphine / acetonitrile / 3 h / 20 °C

14.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.33 h / -78 °C

14.2: trisyl azide / tetrahydrofuran / 0.17 h / -78 °C

14.3: 20 percent / acetic acid / 1 h / -78 - 20 °C

15.1: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 20 °C

16.1: hydrogen; Pd(OH)2 / methanol / 0.5 h

17.1: 31 mg / aq. K₂CO₃ / tetrahydrofuran / 2.5 h / 20 °C

18.1: aq. NaIO₄ / ruthenium(III) chloride hydrate / CCl₄; acetonitrile / 3 h

19.1: 12 mg / diethyl ether

With 1H-imidazole; hydrogenchloride; Trimethyl orthoacetate; dmap; palladium dihydroxide; sodium periodate; n-butyllithium; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; dimethylsulfide; 5A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; trifluoroacetic acid; copper(I) bromide; potassium hexacyanoferrate(III); ruthenium trichloride; potassium osmate(VI); In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Sharpless oxidation;

Reference yield:

(R)-2-Pent-4-enyl-oxirane (180037-71-2) → (2S,6S,8S)-methyl-8-[N-(tert-butoxycarbonyl)amino]-9-oxo-1-azabicyclo[4.3.0]nonane-2-carboxylate (524958-63-2)

Guidance literature:

Multi-step reaction with 18 steps

1.1: (DHQD)2*PYR; K₃Fe(CN)6; aq. K₂CO₃ / K₂OsO₄*2H₂O / 2-methyl-propan-2-ol; H₂O / 14 h / 20 °C

2.1: molecular sieves 5 Angstroem; PPTS / CH₂Cl₂ / 20 h / 20 °C

3.1: coprous bromide; dimethyl sulfide / tetrahydrofuran / 1.5 h / -78 - 30 °C

4.1: aq. HCl / tetrahydrofuran / 2 h / 20 °C

5.1: imidazole / dimethylformamide / 5 h / 20 °C

6.1: triethylamine; 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 48 h / 20 °C

7.1: 48 h / 70 °C

8.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 20 °C

8.2: 81 percent / aq. NaOH; H₂O₂ / 1 h / 20 °C

9.1: hydrogen; Pd(OH)2 / methanol / 1 h

10.1: 675 mg / aq. K₂CO₃ / tetrahydrofuran / 5 h / 20 °C

11.1: aq. NaIO₄ / ruthenium(III) chloride hydrate / CCl₄; acetonitrile / 3 h

12.1: trifluoroacetic acid / CH₂Cl₂ / 1 h

12.2: 337 mg / 2,2'-dipyridinyl disulfide; triphenylphosphine / acetonitrile / 3 h / 20 °C

13.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.33 h / -78 °C

13.2: trisyl azide / tetrahydrofuran / 0.17 h / -78 °C

13.3: 20 percent / acetic acid / 1 h / -78 - 20 °C

14.1: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 20 °C

15.1: hydrogen; Pd(OH)2 / methanol / 0.5 h

16.1: 31 mg / aq. K₂CO₃ / tetrahydrofuran / 2.5 h / 20 °C

17.1: aq. NaIO₄ / ruthenium(III) chloride hydrate / CCl₄; acetonitrile / 3 h

18.1: 12 mg / diethyl ether

With 1H-imidazole; hydrogenchloride; dmap; palladium dihydroxide; sodium periodate; n-butyllithium; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; dimethylsulfide; 5A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; trifluoroacetic acid; copper(I) bromide; potassium hexacyanoferrate(III); ruthenium trichloride; potassium osmate(VI); In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

Reference yield:

(2R,6R)-6,7-epoxyheptane-1,2-diol (524958-49-4) → (2S,6S,8S)-methyl-8-[N-(tert-butoxycarbonyl)amino]-9-oxo-1-azabicyclo[4.3.0]nonane-2-carboxylate (524958-63-2)

Guidance literature:

Multi-step reaction with 17 steps

1.1: molecular sieves 5 Angstroem; PPTS / CH₂Cl₂ / 20 h / 20 °C

2.1: coprous bromide; dimethyl sulfide / tetrahydrofuran / 1.5 h / -78 - 30 °C

3.1: aq. HCl / tetrahydrofuran / 2 h / 20 °C

4.1: imidazole / dimethylformamide / 5 h / 20 °C

5.1: triethylamine; 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 48 h / 20 °C

6.1: 48 h / 70 °C

7.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 20 °C

7.2: 81 percent / aq. NaOH; H₂O₂ / 1 h / 20 °C

8.1: hydrogen; Pd(OH)2 / methanol / 1 h

9.1: 675 mg / aq. K₂CO₃ / tetrahydrofuran / 5 h / 20 °C

10.1: aq. NaIO₄ / ruthenium(III) chloride hydrate / CCl₄; acetonitrile / 3 h

11.1: trifluoroacetic acid / CH₂Cl₂ / 1 h

11.2: 337 mg / 2,2'-dipyridinyl disulfide; triphenylphosphine / acetonitrile / 3 h / 20 °C

12.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.33 h / -78 °C

12.2: trisyl azide / tetrahydrofuran / 0.17 h / -78 °C

12.3: 20 percent / acetic acid / 1 h / -78 - 20 °C

13.1: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 20 °C

14.1: hydrogen; Pd(OH)2 / methanol / 0.5 h

15.1: 31 mg / aq. K₂CO₃ / tetrahydrofuran / 2.5 h / 20 °C

16.1: aq. NaIO₄ / ruthenium(III) chloride hydrate / CCl₄; acetonitrile / 3 h

17.1: 12 mg / diethyl ether

With 1H-imidazole; hydrogenchloride; dmap; palladium dihydroxide; sodium periodate; n-butyllithium; dimethylsulfide; 5A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; trifluoroacetic acid; copper(I) bromide; ruthenium trichloride; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

di-tert-butyl dicarbonate

diazomethane

(R)-5-heptene-1,2-diol

(R)-2-Pent-4-enyl-oxirane