(9R,11S)-11-(4-Dimethylamino-2-methoxy-phenyl)-9-((S)-2-hydroxy-2-hydroxymethyl-butyl)-5,8,9,10,11,12-hexahydro-6H-7,12-diaza-cyclonona[a]indene-7,11-dicarboxylic acid 11-methyl ester 7-(4-nitro-benzyl) ester

Base Information

• Chemical Name: (9R,11S)-11-(4-Dimethylamino-2-methoxy-phenyl)-9-((S)-2-hydroxy-2-hydroxymethyl-butyl)-5,8,9,10,11,12-hexahydro-6H-7,12-diaza-cyclonona[a]indene-7,11-dicarboxylic acid 11-methyl ester 7-(4-nitro-benzyl) ester
• CAS No.: 141521-27-9
• Molecular Formula: C₃₈H₄₆N₄O₉
• Molecular Weight: 702.805
• Mol file: 141521-27-9.mol

Synonyms:(9R,11S)-11-(4-Dimethylamino-2-methoxy-phenyl)-9-((S)-2-hydroxy-2-hydroxymethyl-butyl)-5,8,9,10,11,12-hexahydro-6H-7,12-diaza-cyclonona[a]indene-7,11-dicarboxylic acid 11-methyl ester 7-(4-nitro-benzyl) ester

Chemical Property of (9R,11S)-11-(4-Dimethylamino-2-methoxy-phenyl)-9-((S)-2-hydroxy-2-hydroxymethyl-butyl)-5,8,9,10,11,12-hexahydro-6H-7,12-diaza-cyclonona[a]indene-7,11-dicarboxylic acid 11-methyl ester 7-(4-nitro-benzyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (9R,11S)-11-(4-Dimethylamino-2-methoxy-phenyl)-9-((S)-2-hydroxy-2-hydroxymethyl-butyl)-5,8,9,10,11,12-hexahydro-6H-7,12-diaza-cyclonona[a]indene-7,11-dicarboxylic acid 11-methyl ester 7-(4-nitro-benzyl) ester

There total 39 articles about (9R,11S)-11-(4-Dimethylamino-2-methoxy-phenyl)-9-((S)-2-hydroxy-2-hydroxymethyl-butyl)-5,8,9,10,11,12-hexahydro-6H-7,12-diaza-cyclonona[a]indene-7,11-dicarboxylic acid 11-methyl ester 7-(4-nitro-benzyl) 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: 75.0%

(R)-11-(4-Dimethylamino-2-methoxy-phenyl)-9-((S)-2-ethyl-1,4-dioxa-spiro[4.5]dec-2-ylmethyl)-5,8,9,10,11,12-hexahydro-6H-7,12-diaza-cyclonona[a]indene-7,11-dicarboxylic acid 11-methyl ester 7-(4-nitro-benzyl) ester → (9R,11R)-11-(4-Dimethylamino-2-methoxy-phenyl)-9-((S)-2-hydroxy-2-hydroxymethyl-butyl)-5,8,9,10,11,12-hexahydro-6H-7,12-diaza-cyclonona[a]indene-7,11-dicarboxylic acid 11-methyl ester 7-(4-nitro-benzyl) ester + (9R,11S)-11-(4-Dimethylamino-2-methoxy-phenyl)-9-((S)-2-hydroxy-2-hydroxymethyl-butyl)-5,8,9,10,11,12-hexahydro-6H-7,12-diaza-cyclonona[a]indene-7,11-dicarboxylic acid 11-methyl ester 7-(4-nitro-benzyl) ester (141521-27-9)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 20h; Ambient temperature;

Reference yield:

2-Methylene-1-butanol (4435-54-5) → (9R,11S)-11-(4-Dimethylamino-2-methoxy-phenyl)-9-((S)-2-hydroxy-2-hydroxymethyl-butyl)-5,8,9,10,11,12-hexahydro-6H-7,12-diaza-cyclonona[a]indene-7,11-dicarboxylic acid 11-methyl ester 7-(4-nitro-benzyl) ester (141521-27-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 3A molecular sieves, D-(-)-diethyl tartrate (D-(-)-DET), titanium(IV) isopropoxide, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 4.5 h / -20 °C

2: 1.0 N aq. N NaOH / dioxane / 4.5 h / Heating

3: Amberlyst-H₁₅ / tetrahydrofuran / 7 h / Ambient temperature

4: m-chloroperbenzoic acid / CH₂Cl₂ / Ambient temperature

5: AcONa / 6 h / Heating

6: K₂CO₃ / methanol / 4 h / Heating

7: 75 percent / N-ethylpiperidine, Sn(OTf)2 / tetrahydrofuran / 10 h / Ambient temperature

8: 91 percent / Et₃N / CH₂Cl₂ / 5 h / Ambient temperature

9: 88 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 0.23 h / Ambient temperature

10: Raney nickel / acetone

11: H₂ / 10percent Pt/C / methanol / 760 Torr / Ambient temperature

12: 74 percent / 2,6-di-tert-butyl-4-methylpyridine / nitromethane / 108 h / 23 °C

13: 71 percent / 2.0 M aq. HCl / tetrahydrofuran / 20 h / Ambient temperature

With 1-ethyl-piperidine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium hydroxide; tin(II) trifluoromethanesulfonate; 2,6-di-tert-butyl-4-methylpyridine; diethyl (2S,3S)-tartrate; 3 A molecular sieve; Amberlyst-H₁₅; hydrogen; sodium acetate; nickel; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; platinum on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; 2,2,4-trimethylpentane; nitromethane; dichloromethane; acetone;

Reference yield:

(R)-(2-ethoxyoxiran-2-yl)methanol (121464-71-9) → (9R,11S)-11-(4-Dimethylamino-2-methoxy-phenyl)-9-((S)-2-hydroxy-2-hydroxymethyl-butyl)-5,8,9,10,11,12-hexahydro-6H-7,12-diaza-cyclonona[a]indene-7,11-dicarboxylic acid 11-methyl ester 7-(4-nitro-benzyl) ester (141521-27-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.0 N aq. N NaOH / dioxane / 4.5 h / Heating

2: Amberlyst-H₁₅ / tetrahydrofuran / 7 h / Ambient temperature

3: m-chloroperbenzoic acid / CH₂Cl₂ / Ambient temperature

4: AcONa / 6 h / Heating

5: K₂CO₃ / methanol / 4 h / Heating

6: 75 percent / N-ethylpiperidine, Sn(OTf)2 / tetrahydrofuran / 10 h / Ambient temperature

7: 91 percent / Et₃N / CH₂Cl₂ / 5 h / Ambient temperature

8: 88 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 0.23 h / Ambient temperature

9: Raney nickel / acetone

10: H₂ / 10percent Pt/C / methanol / 760 Torr / Ambient temperature

11: 74 percent / 2,6-di-tert-butyl-4-methylpyridine / nitromethane / 108 h / 23 °C

12: 71 percent / 2.0 M aq. HCl / tetrahydrofuran / 20 h / Ambient temperature

With 1-ethyl-piperidine; hydrogenchloride; sodium hydroxide; tin(II) trifluoromethanesulfonate; 2,6-di-tert-butyl-4-methylpyridine; Amberlyst-H₁₅; hydrogen; sodium acetate; nickel; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; platinum on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; nitromethane; dichloromethane; acetone;

upstream raw materials:

(S)-11-(4-Dimethylamino-2-methoxy-phenyl)-9-((S)-2-ethyl-1,4-dioxa-spiro[4.5]dec-2-ylmethyl)-5,8,9,10,11,12-hexahydro-6H-7,12-diaza-cyclonona[a]indene-7,11-dicarboxylic acid 11-methyl ester 7-(4-nitro-benzyl) ester

2-Methylene-1-butanol

(-)-(9R,2S,2'S)-3H-9-(methoxycarbonyl)-2-(2'-ethyl-2',3'dihydroxypropyl)hexahydroindolizino<8,7-b>indole cyclohexylidene ketal

(R)-(2-ethoxyoxiran-2-yl)methanol

Downstream raw materials:

(9S,11S)-11-(4-Dimethylamino-2-methoxy-phenyl)-9-((S)-2-formyl-2-hydroxy-butyl)-5,8,9,10,11,12-hexahydro-6H-7,12-diaza-cyclonona[a]indene-7,11-dicarboxylic acid 11-methyl ester 7-(4-nitro-benzyl) ester

C₃₀H₃₉N₃O₄

(9R,11S)-11-(4-Dimethylamino-2-methoxy-phenyl)-9-((S)-2-formyl-2-hydroxy-butyl)-5,8,9,10,11,12-hexahydro-6H-7,12-diaza-cyclonona[a]indene-7,11-dicarboxylic acid 11-methyl ester 7-(4-nitro-benzyl) ester

Refernces

• 1、 Magnus, Philip,Mendoza, José S.,Stamford, Andrew,Ladlow, Mark,Willis, Paul. "Nonoxidative coupling methodology for the synthesis of the antitumor bisindole alkaloid vinblastine and a lower-half analogue: Solvent effect on the stereochemistry of the crucial C-15/C-18′ bond". . p. 10232 - 10245. Retrieved 2007/10/02.