(1R,7R,8S)-2-{(E)-2-[(tert-Butyldimethylsilyl)oxy]ethylidene}-7-(2-nitrophenyl)-4-azatricyclo[5.2.2.0^4,8]undecan-11-one

Base Information

• Chemical Name: (1R,7R,8S)-2-{(E)-2-[(tert-Butyldimethylsilyl)oxy]ethylidene}-7-(2-nitrophenyl)-4-azatricyclo[5.2.2.0^4,8]undecan-11-one
• CAS No.: 222162-02-9
• Molecular Formula: C₂₄H₃₄N₂O₄Si
• Molecular Weight: 442.63

Synonyms:(1R,7R,8S)-2-{(E)-2-[(tert-Butyldimethylsilyl)oxy]ethylidene}-7-(2-nitrophenyl)-4-azatricyclo[5.2.2.0^4,8]undecan-11-one

Chemical Property of (1R,7R,8S)-2-{(E)-2-[(tert-Butyldimethylsilyl)oxy]ethylidene}-7-(2-nitrophenyl)-4-azatricyclo[5.2.2.0^4,8]undecan-11-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,7R,8S)-2-{(E)-2-[(tert-Butyldimethylsilyl)oxy]ethylidene}-7-(2-nitrophenyl)-4-azatricyclo[5.2.2.0^4,8]undecan-11-one

There total 13 articles about (1R,7R,8S)-2-{(E)-2-[(tert-Butyldimethylsilyl)oxy]ethylidene}-7-(2-nitrophenyl)-4-azatricyclo[5.2.2.0^4,8]undecan-11-one 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: 53.0%

(3aR,7aS)-1-{(Z)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodo-2-butenyl}-3a-(2-nitrophenyl)-1,2,3,3a,7,7a-hexahydroindol-4-one (222162-01-8) → (1R,7R,8S)-2-{(E)-2-[(tert-Butyldimethylsilyl)oxy]ethylidene}-7-(2-nitrophenyl)-4-azatricyclo[5.2.2.04,8]undecan-11-one (222162-02-9)

Guidance literature:

With triethylamine; triphenylphosphine; palladium diacetate; at 90 ℃;

DOI:10.1002/(SICI)1521-3773(19990201)38:3<395::AID-ANIE395>3.0.CO;2-5

Reference yield:

o-nitroiodobenzene (609-73-4) → (1R,7R,8S)-2-{(E)-2-[(tert-Butyldimethylsilyl)oxy]ethylidene}-7-(2-nitrophenyl)-4-azatricyclo[5.2.2.04,8]undecan-11-one (222162-02-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 72 percent / K₂CO₃ / dimethylsulfoxide / 85 - 90 °C

2: 85 percent / K₂CO₃ / acetone / Heating

3: 80 percent / toluene / 180 - 190 °C

4: 1.) O₃, 2.) NaBH₃CN / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, i-PrOH

5: 72 percent / 135 °C

6: HN(SiMe₃)2 / CH₂Cl₂; pentane / -20 °C

7: (PhSe)2 / tetrahydrofuran

8: 1.) O₃, 2.) i-Pr₂NH / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

9: methanol / Heating

10: K₂CO₃, LiI / acetonitrile / 50 °C

11: 53 percent / PPh₃, Et₃N / Pd(OAc)2 / 90 °C

With diphenyl diselenide; sodium cyanoborohydride; potassium carbonate; ozone; triethylamine; diisopropylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium iodide; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetone; toluene; acetonitrile; pentane;

DOI:10.1002/(SICI)1521-3773(19990201)38:3<395::AID-ANIE395>3.0.CO;2-5

Reference yield:

1,3-cylohexanedione (504-02-9) → (1R,7R,8S)-2-{(E)-2-[(tert-Butyldimethylsilyl)oxy]ethylidene}-7-(2-nitrophenyl)-4-azatricyclo[5.2.2.04,8]undecan-11-one (222162-02-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 72 percent / K₂CO₃ / dimethylsulfoxide / 85 - 90 °C

2: 85 percent / K₂CO₃ / acetone / Heating

3: 80 percent / toluene / 180 - 190 °C

4: 1.) O₃, 2.) NaBH₃CN / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, i-PrOH

5: 72 percent / 135 °C

6: HN(SiMe₃)2 / CH₂Cl₂; pentane / -20 °C

7: (PhSe)2 / tetrahydrofuran

8: 1.) O₃, 2.) i-Pr₂NH / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

9: methanol / Heating

10: K₂CO₃, LiI / acetonitrile / 50 °C

11: 53 percent / PPh₃, Et₃N / Pd(OAc)2 / 90 °C

With diphenyl diselenide; sodium cyanoborohydride; potassium carbonate; ozone; triethylamine; diisopropylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium iodide; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetone; toluene; acetonitrile; pentane;

DOI:10.1002/(SICI)1521-3773(19990201)38:3<395::AID-ANIE395>3.0.CO;2-5

upstream raw materials:

(3aR,7aS)-1-{(Z)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodo-2-butenyl}-3a-(2-nitrophenyl)-1,2,3,3a,7,7a-hexahydroindol-4-one

o-nitroiodobenzene

1,3-cylohexanedione

3-hydroxy-2-(2-nitrophenyl)cyclohex-2-enone

Downstream raw materials:

(17R,19E)-17,18-epoxy-cur-19-en-17-ol

strychnidin-10-one

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