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

Base Information

• Chemical Name: 3β-(chloromethyl)-17β-hydroxy-5-aza-A-nor-B-homoandrostan-6-one benzoate
• CAS No.: 138415-97-1
• Molecular Formula: C₂₆H₃₄ClNO₃
• Molecular Weight: 444.014
• Mol file: 138415-97-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 3β-(chloromethyl)-17β-hydroxy-5-aza-A-nor-B-homoandrostan-6-one benzoate 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: 81.0%

Benzoic acid (1S,3aS,3bS,8S,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 (138415-93-7) → 3α-chloro-17β-hydroxy-5-aza-B-homoandrostan-6-one benzoate (138415-94-8) + 3β-(chloromethyl)-17β-hydroxy-5-aza-A-nor-B-homoandrostan-6-one benzoate (138415-97-1)

Guidance literature:

With lithium chloride; In acetone; tert-butyl alcohol; for 48h; Yields of byproduct given; Heating;

DOI:10.1016/0040-4039(91)80208-N

Reference yield: 14.0%

3β,17β-dihydroxy-5-aza-B-homoandrostan-6-one 17-benzoate (138415-91-5) → 3α-chloro-17β-hydroxy-5-aza-B-homoandrostan-6-one benzoate (138415-94-8) + 3β-(chloromethyl)-17β-hydroxy-5-aza-A-nor-B-homoandrostan-6-one benzoate (138415-97-1)

Guidance literature:

With thionyl chloride; In dichloromethane; for 60h; Ambient temperature;

DOI:10.1016/0040-4039(91)80208-N DOI:10.1021/jo00041a013

Reference yield:

17β-hydroxy-5-oxo-4,5-seco-androst-3-yne (17541-44-5) → 3β-(chloromethyl)-17β-hydroxy-5-aza-A-nor-B-homoandrostan-6-one benzoate (138415-97-1)

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: 100 percent / n-Bu₄NF / tetrahydrofuran

9: 63 percent / SOCl₂ / CH₂Cl₂ / 60 h / Ambient temperature

With pyridine; 1H-imidazole; quinoline; dmap; thionyl chloride; 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; dichloromethane; chloroform;

DOI:10.1021/jo00041a013

upstream raw materials:

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

Benzoic acid (1S,3aS,3bS,8S,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

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

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