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

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Chemical Name:2-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)aziridine-1-carboxylic acid tert-butyl ester
CAS No.:331821-36-4
Molecular Formula:C₁₈H₂₁NO₄
Molecular Weight:315.369
Hs Code.:

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

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

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

There total 10 articles about 2-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)aziridine-1-carboxylic 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: 91.0%

: 331821-73-9
[1R,4S,5S,6S,4(1'S)]-[2'-hydroxy-1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)ethyl]carbamic acid tert-butyl ester

: 331821-36-4
2-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)aziridine-1-carboxylic acid tert-butyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 3.5h;
DOI:10.1021/jo001257i

Reference yield:

: 536-74-3
phenylacetylene

: 331821-36-4
2-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)aziridine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

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

1.2: 8 percent / tetrahydrofuran; hexane / 2.25 h / -78 °C

2.1: 78 percent / Red-Al / diethyl ether / 0.92 h / 0 - 20 °C

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

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

5.1: 71 percent / Cu(TBS)2 / toluene / Heating

6.1: aq. HCl; triethylsilane / dioxane / 1 h

7.1: 2.61 g / Et₃N / acetonitrile / 12 h / 20 °C

8.1: 91 percent / DEAD; PPh₃ / tetrahydrofuran / 3.5 h / 20 °C

With hydrogenchloride; triethylsilane; n-butyllithium; 18-crown-6 ether; N,N-dimethyl-aniline; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; diethylazodicarboxylate; Cu(TBS)2; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; toluene; acetonitrile; 8.1: Mitsunobu cyclization;
DOI:10.1021/jo001257i

Reference yield:

: 154437-23-7
trans-[4S,4(1'S)]-4-(1'-hydroxy-3'-phenyl-2'-propenyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 331821-36-4
2-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)aziridine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

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

2: Et₃N / CH₂Cl₂ / 0.42 h / 0 - 20 °C

3: 71 percent / Cu(TBS)2 / toluene / Heating

4: aq. HCl; triethylsilane / dioxane / 1 h

5: 2.61 g / Et₃N / acetonitrile / 12 h / 20 °C

6: 91 percent / DEAD; PPh₃ / tetrahydrofuran / 3.5 h / 20 °C

With hydrogenchloride; triethylsilane; N,N-dimethyl-aniline; triethylamine; triphenylphosphine; diethylazodicarboxylate; Cu(TBS)2; In tetrahydrofuran; 1,4-dioxane; dichloromethane; toluene; acetonitrile; 6: Mitsunobu cyclization;
DOI:10.1021/jo001257i