(+/-)-5,8,9,10,11,14-hexahydro-6H-15,16-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dicarboxylic acid 13-methyl ester 7-phenyl ester

Base Information

• Chemical Name: (+/-)-5,8,9,10,11,14-hexahydro-6H-15,16-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dicarboxylic acid 13-methyl ester 7-phenyl ester
• CAS No.: 322765-43-5
• Molecular Formula: C₂₇H₃₀N₂O₆
• Molecular Weight: 478.545
• Mol file: 322765-43-5.mol

Synonyms:(+/-)-5,8,9,10,11,14-hexahydro-6H-15,16-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dicarboxylic acid 13-methyl ester 7-phenyl ester

Chemical Property of (+/-)-5,8,9,10,11,14-hexahydro-6H-15,16-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dicarboxylic acid 13-methyl ester 7-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-5,8,9,10,11,14-hexahydro-6H-15,16-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dicarboxylic acid 13-methyl ester 7-phenyl ester

There total 14 articles about (+/-)-5,8,9,10,11,14-hexahydro-6H-15,16-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dicarboxylic acid 13-methyl ester 7-phenyl 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: 47.0%

phenyl chloroformate (1885-14-9) + C20H26N2O4 (322765-42-4) → (+/-)-5,8,9,10,11,14-hexahydro-6H-15,16-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dicarboxylic acid 13-methyl ester 7-phenyl ester (322765-43-5)

Guidance literature:

In dichloromethane; for 48h; Heating;

DOI:10.1016/S0040-4020(02)00243-0

Reference yield:

2-nitroveratraldehyde (55149-84-3) → (+/-)-5,8,9,10,11,14-hexahydro-6H-15,16-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dicarboxylic acid 13-methyl ester 7-phenyl ester (322765-43-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: KOH / dimethylformamide; ethanol

1.2: 73 percent / Ac₂O; NaOAc / Heating

2.1: 85 percent / Fe / acetic acid; ethanol / 95 °C

3.1: 92 percent / POCl₃ / 0 - 25 °C

4.1: 100 percent / NH₄OAc / 0.67 h / Heating

5.1: 91 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

6.1: 2.0 g / molecular sieves 4 Angstroem; trifluoroacetic acid / CH₂Cl₂ / 0 - 23 °C

7.1: 67 percent / 1-hydroxybenzotriazole monohydrate; EDCI; Et₃N / dimethylformamide / 25 h / 0 - 20 °C

8.1: 100 percent / Bellau's reagent / tetrahydrofuran / 15 h / 0 - 23 °C

9.1: 77 percent / NiCl₂*6H₂O; NaBH₄ / tetrahydrofuran; methanol / 0.08 h / 0 °C

10.1: 47 percent / CH₂Cl₂ / 48 h / Heating

With potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; 4 A molecular sieve; ammonium acetate; iron; 2,4-(4-phenoxyphenyl)-1,3-dithia-2λ(5),4λ(5)-diphosphetane 2,4-disulfides; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; nickel dichloride; trichlorophosphate; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; 1.1: Henry reaction / 3.1: Vilsmeier formylation / 4.1: Henry reaction / 6.1: Pictet Spengler reaction;

DOI:10.1016/S0040-4020(02)00243-0

Reference yield:

6,7-dimethoxy-1H-indole (31165-13-6) → (+/-)-5,8,9,10,11,14-hexahydro-6H-15,16-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dimethoxy-7,14-diazacycloundeca[a]indene-7,13-dicarboxylic acid 13-methyl ester 7-phenyl ester (322765-43-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / POCl₃ / 0 - 25 °C

2: 100 percent / NH₄OAc / 0.67 h / Heating

3: 91 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

4: 2.0 g / molecular sieves 4 Angstroem; trifluoroacetic acid / CH₂Cl₂ / 0 - 23 °C

5: 67 percent / 1-hydroxybenzotriazole monohydrate; EDCI; Et₃N / dimethylformamide / 25 h / 0 - 20 °C

6: 100 percent / Bellau's reagent / tetrahydrofuran / 15 h / 0 - 23 °C

7: 77 percent / NiCl₂*6H₂O; NaBH₄ / tetrahydrofuran; methanol / 0.08 h / 0 °C

8: 47 percent / CH₂Cl₂ / 48 h / Heating

With sodium tetrahydroborate; lithium aluminium tetrahydride; 4 A molecular sieve; ammonium acetate; 2,4-(4-phenoxyphenyl)-1,3-dithia-2λ(5),4λ(5)-diphosphetane 2,4-disulfides; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; nickel dichloride; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Vilsmeier formylation / 2: Henry reaction / 4: Pictet Spengler reaction;

DOI:10.1016/S0040-4020(02)00243-0

upstream raw materials:

phenyl chloroformate

C₂₀H₂₆N₂O₄

6,7-dimethoxy-1H-indole

2-nitroveratraldehyde