1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)propyl-1'-carbamic acid tert-butyl ester

Base Information

• Chemical Name: 1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)propyl-1'-carbamic acid tert-butyl ester
• CAS No.: 331821-17-1
• Molecular Formula: C₁₉H₂₅NO₄
• Molecular Weight: 331.412

Synonyms:1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)propyl-1'-carbamic acid tert-butyl ester

Chemical Property of 1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)propyl-1'-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)propyl-1'-carbamic acid tert-butyl ester

There total 11 articles about 1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)propyl-1'-carbamic acid tert-butyl 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: 90.0%

methyllithium (917-54-4) + 2'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)aziridine-1-carboxylic acid tert-butyl ester (331821-14-8) → 1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)propyl-1'-carbamic acid tert-butyl ester (331821-17-1)

Guidance literature:

methyllithium; With copper(I) bromide dimethylsulfide complex; In diethyl ether; at 0 ℃;

2'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)aziridine-1-carboxylic acid tert-butyl ester; In diethyl ether; dichloromethane; at 0 - 20 ℃; for 0.166667h; Further stages.;

DOI:10.1021/jo001257i

Reference yield:

phenylacetylene (536-74-3) → 1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)propyl-1'-carbamic acid tert-butyl ester (331821-17-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-BuLi; 18-crown-6 / tetrahydrofuran; hexane / 1.17 h / -78 °C

1.2: 76 percent / tetrahydrofuran; hexane / 2.25 h / -78 °C

2.1: 87 percent / H₂; ethylenediamine / P-2 Ni / ethanol

3.1: N,N-dimethylaniline / CH₂Cl₂ / 0.25 h / 0 °C

4.1: 516 mg / Et₃N / CH₂Cl₂ / 0.42 h / 0 - 20 °C

5.1: Cu(TBS)2 / toluene / Heating

6.1: conc. HCl; triethylsilane / tetrahydrofuran / 6 h / 70 °C

7.1: 720 mg / Et₃N / acetonitrile / 20 °C

8.1: 74 percent / DEAD; PPh₃ / tetrahydrofuran / 3.5 h / 20 °C

9.1: CuBr*DMS / diethyl ether / 0 °C

9.2: 90 percent / diethyl ether; CH₂Cl₂ / 0.17 h / 0 - 20 °C

With hydrogenchloride; triethylsilane; n-butyllithium; copper(I) bromide dimethylsulfide complex; 18-crown-6 ether; hydrogen; N,N-dimethyl-aniline; ethylenediamine; triethylamine; triphenylphosphine; diethylazodicarboxylate; Cu(TBS)2; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile; 8.1: Mitsunobu cyclization;

DOI:10.1021/jo001257i

Reference yield:

tert-butyl (4S)-4-<(1R)-1-hydroxy-3-phenyl-2-propynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (241478-33-1) → 1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)propyl-1'-carbamic acid tert-butyl ester (331821-17-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 87 percent / H₂; ethylenediamine / P-2 Ni / ethanol

2.1: N,N-dimethylaniline / CH₂Cl₂ / 0.25 h / 0 °C

3.1: 516 mg / Et₃N / CH₂Cl₂ / 0.42 h / 0 - 20 °C

4.1: Cu(TBS)2 / toluene / Heating

5.1: conc. HCl; triethylsilane / tetrahydrofuran / 6 h / 70 °C

6.1: 720 mg / Et₃N / acetonitrile / 20 °C

7.1: 74 percent / DEAD; PPh₃ / tetrahydrofuran / 3.5 h / 20 °C

8.1: CuBr*DMS / diethyl ether / 0 °C

8.2: 90 percent / diethyl ether; CH₂Cl₂ / 0.17 h / 0 - 20 °C

With hydrogenchloride; triethylsilane; copper(I) bromide dimethylsulfide complex; hydrogen; N,N-dimethyl-aniline; ethylenediamine; triethylamine; triphenylphosphine; diethylazodicarboxylate; Cu(TBS)2; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; toluene; acetonitrile; 7.1: Mitsunobu cyclization;

DOI:10.1021/jo001257i

upstream raw materials:

methyllithium

2'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)aziridine-1-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

phenylacetylene

Downstream raw materials:

[1S,2R,3S,2(1'R,2'S)]-2-[1'-(tert-butyldimethylsilanyloxy)-2'-(tert-butoxycarbonylamino)butyl]-3-phenylcyclopropane-1-carboxylic acid

[1R,2R,3S,2(1'R,2'S)]-2-[1'-(tert-butyldimethylsilanyloxy)-2'-(tert-butoxycarbonylamino)butyl]-3-phenylcyclopropane-1-carboxylic acid N-methoxy-N-methylamide

[1S,2R,3S,2(1'R,2'S)]-2-[1'-(tert-butyldimethylsilanyloxy)-2'-(tert-butoxycarbonylamino)butyl]-3-phenylcyclopropane-1-carbonyl-L-methionine methyl ester

(R)-4-((S)-1-{(R)-Hydroxy-[(1R,2R,3S)-2-((S)-1-methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-3-phenyl-cyclopropyl]-methyl}-propylcarbamoyl)-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

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