Benzoic acid (1S,3aS,3bS,8R,10aR,10bS,12aS)-10a,12a-dimethyl-6-oxo-8-(toluene-4-sulfonyloxy)-hexadecahydro-6a-aza-benzo[3,4]cyclohepta[1,2-e]inden-1-yl ester

Base Information

• Chemical Name: Benzoic acid (1S,3aS,3bS,8R,10aR,10bS,12aS)-10a,12a-dimethyl-6-oxo-8-(toluene-4-sulfonyloxy)-hexadecahydro-6a-aza-benzo[3,4]cyclohepta[1,2-e]inden-1-yl ester
• CAS No.: 138415-92-6
• Molecular Formula: C₃₃H₄₁NO₆S
• Molecular Weight: 579.758
• Mol file: 138415-92-6.mol

Synonyms:Benzoic acid (1S,3aS,3bS,8R,10aR,10bS,12aS)-10a,12a-dimethyl-6-oxo-8-(toluene-4-sulfonyloxy)-hexadecahydro-6a-aza-benzo[3,4]cyclohepta[1,2-e]inden-1-yl ester

Chemical Property of Benzoic acid (1S,3aS,3bS,8R,10aR,10bS,12aS)-10a,12a-dimethyl-6-oxo-8-(toluene-4-sulfonyloxy)-hexadecahydro-6a-aza-benzo[3,4]cyclohepta[1,2-e]inden-1-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1S,3aS,3bS,8R,10aR,10bS,12aS)-10a,12a-dimethyl-6-oxo-8-(toluene-4-sulfonyloxy)-hexadecahydro-6a-aza-benzo[3,4]cyclohepta[1,2-e]inden-1-yl ester

There total 10 articles about Benzoic acid (1S,3aS,3bS,8R,10aR,10bS,12aS)-10a,12a-dimethyl-6-oxo-8-(toluene-4-sulfonyloxy)-hexadecahydro-6a-aza-benzo[3,4]cyclohepta[1,2-e]inden-1-yl 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: 7.0%

3α,17β-dihydroxy-5-aza-B-homoandrostan-6-one 17-benzoate (138415-90-4) + p-toluenesulfonyl chloride (98-59-9) → 3α-(chloromethyl)-17β-hydroxy-5-aza-A-nor-B-homoandrostan-6-one benzoate (138415-96-0) + Benzoic acid (1S,3aS,3bS,8R,10aR,10bS,12aS)-10a,12a-dimethyl-6-oxo-8-(toluene-4-sulfonyloxy)-hexadecahydro-6a-aza-benzo[3,4]cyclohepta[1,2-e]inden-1-yl ester (138415-92-6)

Guidance literature:

With pyridine; for 20h;

DOI:10.1021/jo00041a013

Reference yield:

17β-hydroxy-5-oxo-4,5-seco-androst-3-yne (17541-44-5) → Benzoic acid (1S,3aS,3bS,8R,10aR,10bS,12aS)-10a,12a-dimethyl-6-oxo-8-(toluene-4-sulfonyloxy)-hexadecahydro-6a-aza-benzo[3,4]cyclohepta[1,2-e]inden-1-yl ester (138415-92-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 4-(N,N-dimethylamino)pyridine, pyridine / 12 h / Ambient temperature

2: H₂, quinoline / 5percent Pd/CaCO₃/Pb / aq. ethanol / 760 Torr

3: 81 percent / NH₂OH*HCl, pyridine / methanol / Heating

4: 45 percent / p-TsCl, 4-(N,N-dimethylamino)pyridine, pyridine / 65 °C

5: 96 percent / MCPBA / CHCl₃

6: 1) NaI, 2) imidazole / 1) THF, 2 h, 2) DMF, 48 h

7: 1) NaH, 2) AcOH / 1) mineral oil, THF, r.t., 3 h, 2) mineral oil, THF, 0 deg C

8: 95 percent / n-Bu₄NF / tetrahydrofuran / 2 h

9: 79 percent / pyridine / 20 h

With pyridine; 1H-imidazole; quinoline; dmap; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; acetic acid; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; sodium iodide; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; chloroform;

DOI:10.1021/jo00041a013

Reference yield:

17β-hydroxy-4,5-secoandrost-3-yn-5-one benzoate (99463-59-9) → Benzoic acid (1S,3aS,3bS,8R,10aR,10bS,12aS)-10a,12a-dimethyl-6-oxo-8-(toluene-4-sulfonyloxy)-hexadecahydro-6a-aza-benzo[3,4]cyclohepta[1,2-e]inden-1-yl ester (138415-92-6)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂, quinoline / 5percent Pd/CaCO₃/Pb / aq. ethanol / 760 Torr

2: 81 percent / NH₂OH*HCl, pyridine / methanol / Heating

3: 45 percent / p-TsCl, 4-(N,N-dimethylamino)pyridine, pyridine / 65 °C

4: 96 percent / MCPBA / CHCl₃

5: 1) NaI, 2) imidazole / 1) THF, 2 h, 2) DMF, 48 h

6: 1) NaH, 2) AcOH / 1) mineral oil, THF, r.t., 3 h, 2) mineral oil, THF, 0 deg C

7: 95 percent / n-Bu₄NF / tetrahydrofuran / 2 h

8: 79 percent / pyridine / 20 h

With pyridine; 1H-imidazole; quinoline; dmap; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; acetic acid; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; sodium iodide; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; chloroform;

DOI:10.1021/jo00041a013

upstream raw materials:

3α,17β-dihydroxy-5-aza-B-homoandrostan-6-one 17-benzoate

p-toluenesulfonyl chloride

17β-hydroxy-5-oxo-4,5-seco-androst-3-yne

17β-hydroxy-4,5-secoandrost-3-yn-5-one benzoate

Downstream raw materials:

Benzoic acid (1R,3aR,3bS,5aS,6S,8aS,8bS)-1-hydroxymethyl-3a,5a-dimethyl-11-oxo-hexadecahydro-11a-aza-indeno[5,4-e]azulen-6-yl ester

3β-chloro-17β-hydroxy-5-aza-B-homoandrostan-6-one benzoate

3α-(chloromethyl)-17β-hydroxy-5-aza-A-nor-B-homoandrostan-6-one benzoate