(4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-yl 4-nitrobenzoate

Base Information

• Chemical Name: (4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-yl 4-nitrobenzoate
• CAS No.: 823788-03-0
• Molecular Formula: C₁₈H₂₄N₂O₄
• Molecular Weight: 332.4
• Mol file: 823788-03-0.mol

Synonyms:(4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-yl 4-nitrobenzoate

Chemical Property of (4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-yl 4-nitrobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-yl 4-nitrobenzoate

There total 13 articles about (4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-yl 4-nitrobenzoate 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: 66.0%

4-nitro-benzoic acid (62-23-7) + (4R,4aS,6S,7S,7aR)-2,4,7-trimethyl-octahydro-1H-cyclopenta[c]pyridin-6-ol (824424-10-4) → (4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-yl 4-nitrobenzoate (823788-03-0)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1021/ja0401702

Reference yield:

(1S,2S,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-3-oxocyclopentanecarbaldehyde (823788-10-9) → (4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-yl 4-nitrobenzoate (823788-03-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 71 percent / sodium borohydride / tetrahydrofuran; ethanol / 0.5 h

2: 99 percent / triphenylphosphine; diethyl azidocarboxylate / tetrahydrofuran / 1 h / 20 °C

3: 95 percent / trifluoroacetic acid / CH₂Cl₂ / 16 h / 20 °C

4: 81 percent / K₂CO₃ / acetonitrile / 3 h / Heating

5: 10 percent / palladium(II) acetate; N,N'-bis(benzylidene)ethylenediamine; poly(methylhydrosiloxane) / acetic acid / benzene / 4 h / 95 °C

6: 97 percent / sodium borohydrate / methanol / 0.5 h

7: 93 percent / imidazole / dimethylformamide / 16 h / 20 °C

8: 78 percent / sodium naphthalenide; sodium / 1,2-dimethoxy-ethane / 0.5 h / -50 °C

9: 97 percent / aq. NaBH₃CN / acetonitrile / 0.25 h / 20 °C

10: 84 percent / platinum(II) oxide; H₂ / methanol / 24 h / 3800 Torr

11: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 36 h / 20 °C

12: 66 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 6 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; platinum(II) oxide; N,N'-bis(benzyliden)ethylendiamine; tetrabutyl ammonium fluoride; hydrogen; palladium diacetate; sodium; sodium naphthalenide; sodium cyanoborohydride; potassium carbonate; triphenylphosphine; trifluoroacetic acid; poly(methylhydrosiloxane); diethylazodicarboxylate; acetic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene; 2: Mitsunobu reaction / 12: Mitsunobu reaction;

DOI:10.1021/ja0401702

Reference yield:

(4S)-4-tert-butyldimethylsilyloxycyclopent-2-en-1-one (56745-67-6,61305-35-9,61740-33-8,61305-36-0) → (4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-yl 4-nitrobenzoate (823788-03-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: butyllithium; dimethylzinc / tetrahydrofuran; hexane / 0.25 h / 0 °C

1.2: tetrahydrofuran; hexane / 0.25 h / -78 °C

1.3: 77 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 16 h / -40 °C

2.1: ozone / CH₂Cl₂; methanol / -78 °C

2.2: 96 percent / methyl sulfide / CH₂Cl₂; methanol / 2 h / 20 °C

3.1: 71 percent / sodium borohydride / tetrahydrofuran; ethanol / 0.5 h

4.1: 99 percent / triphenylphosphine; diethyl azidocarboxylate / tetrahydrofuran / 1 h / 20 °C

5.1: 95 percent / trifluoroacetic acid / CH₂Cl₂ / 16 h / 20 °C

6.1: 81 percent / K₂CO₃ / acetonitrile / 3 h / Heating

7.1: 10 percent / palladium(II) acetate; N,N'-bis(benzylidene)ethylenediamine; poly(methylhydrosiloxane) / acetic acid / benzene / 4 h / 95 °C

8.1: 97 percent / sodium borohydrate / methanol / 0.5 h

9.1: 93 percent / imidazole / dimethylformamide / 16 h / 20 °C

10.1: 78 percent / sodium naphthalenide; sodium / 1,2-dimethoxy-ethane / 0.5 h / -50 °C

11.1: 97 percent / aq. NaBH₃CN / acetonitrile / 0.25 h / 20 °C

12.1: 84 percent / platinum(II) oxide; H₂ / methanol / 24 h / 3800 Torr

13.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 36 h / 20 °C

14.1: 66 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 6 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; platinum(II) oxide; N,N'-bis(benzyliden)ethylendiamine; tetrabutyl ammonium fluoride; hydrogen; dimethyl zinc(II); palladium diacetate; sodium; sodium naphthalenide; sodium cyanoborohydride; potassium carbonate; ozone; triphenylphosphine; trifluoroacetic acid; poly(methylhydrosiloxane); diethylazodicarboxylate; acetic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene; 4.1: Mitsunobu reaction / 14.1: Mitsunobu reaction;

DOI:10.1021/ja0401702

upstream raw materials:

4-nitro-benzoic acid

(4R,4aS,6S,7S,7aR)-2,4,7-trimethyl-octahydro-1H-cyclopenta[c]pyridin-6-ol

(4S)-4-tert-butyldimethylsilyloxycyclopent-2-en-1-one

(1S,2S,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-3-oxocyclopentanecarbaldehyde

Downstream raw materials:

(4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-ol