(1R,4R,7R)-7-((1S,2R,6S,7R)-7,10,10-Trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-2-aza-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (1R,4R,7R)-7-((1S,2R,6S,7R)-7,10,10-Trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-2-aza-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid benzyl ester
• CAS No.: 189184-88-1
• Molecular Formula: C₂₆H₃₂N₂O₃
• Molecular Weight: 420.552

Synonyms:(1R,4R,7R)-7-((1S,2R,6S,7R)-7,10,10-Trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-2-aza-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid benzyl ester

Chemical Property of (1R,4R,7R)-7-((1S,2R,6S,7R)-7,10,10-Trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-2-aza-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of (1R,4R,7R)-7-((1S,2R,6S,7R)-7,10,10-Trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-2-aza-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid benzyl ester

There total 1 articles about (1R,4R,7R)-7-((1S,2R,6S,7R)-7,10,10-Trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-2-aza-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid 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: 43.0%

N-benzyloxycarbonyl-1,2-dihydropyridine (79328-85-1) + (1S,2R,6S,7R)-7,10,10-Trimethyl-4-vinyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-ene (129064-36-4) → (1R,4R,7R)-7-((1S,2R,6S,7R)-7,10,10-Trimethyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-en-4-yl)-2-aza-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid benzyl ester (189184-88-1)

Guidance literature:

With trifluoroacetic anhydride; methyloxirane; In dichloromethane; at -78 ℃; for 3h;

DOI:10.1016/S0040-4020(97)00182-8

Reference yield:

(1R,4R,7R)-7-((1S,2R,6S,7R)-7,10,10-Trimethyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-en-4-yl)-2-aza-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid benzyl ester (189184-88-1) → (3S,4R,5S)-5-Dimethylaminomethyl-3,4-dihydroxy-cyclohex-1-enecarboxylic acid tert-butyl ester (189184-81-4)

Guidance literature:

Multi-step reaction with 7 steps

2: 1.) OsO₄, N-methylmorpholine N-oxide, methanesulfonamide, 2.) sodium sulfite / 1.) acetone, t-butanol, 20 deg C, 4 h, 2.) H₂O, 30 min

3: 1.615 g / para-toluenesulfonic acid / 12 h / Ambient temperature

4: 1.) H₂, 2.) H₂ / 1.) 10percent Pd/C / 1.) MeOH, 20 deg C, 2 h, 2.) H₂O, 2 h.

5: 3 h / 20 °C

6: tBuOK / tetrahydrofuran / 2 h / Ambient temperature

7: 81 percent / para-toluenesulfonic acid / 2-methyl-propan-2-ol / 20 h / 60 °C

With osmium(VIII) oxide; methanesulfonamide; potassium tert-butylate; hydrogen; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; sodium sulfite; palladium on activated charcoal; In tetrahydrofuran; tert-butyl alcohol;

DOI:10.1016/S0040-4020(97)00182-8

Reference yield:

(1R,4R,7R)-7-((1S,2R,6S,7R)-7,10,10-Trimethyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-en-4-yl)-2-aza-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid benzyl ester (189184-88-1) → (3S,4R,5S)-5-Dimethylaminomethyl-4-hydroxy-3-prop-2-ynyloxy-cyclohex-1-enecarboxylic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 8 steps

2: 1.) OsO₄, N-methylmorpholine N-oxide, methanesulfonamide, 2.) sodium sulfite / 1.) acetone, t-butanol, 20 deg C, 4 h, 2.) H₂O, 30 min

3: 1.615 g / para-toluenesulfonic acid / 12 h / Ambient temperature

4: 1.) H₂, 2.) H₂ / 1.) 10percent Pd/C / 1.) MeOH, 20 deg C, 2 h, 2.) H₂O, 2 h.

5: 3 h / 20 °C

6: tBuOK / tetrahydrofuran / 2 h / Ambient temperature

7: 81 percent / para-toluenesulfonic acid / 2-methyl-propan-2-ol / 20 h / 60 °C

8: 23 percent / LiHMDS / dimethylformamide; toluene / 3 h / 20 °C

With osmium(VIII) oxide; methanesulfonamide; potassium tert-butylate; hydrogen; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; lithium hexamethyldisilazane; sodium sulfite; palladium on activated charcoal; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4020(97)00182-8

upstream raw materials:

N-benzyloxycarbonyl-1,2-dihydropyridine

(1S,2R,6S,7R)-7,10,10-Trimethyl-4-vinyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene

Downstream raw materials:

(1R,4R,6R)-2-Aza-bicyclo[2.2.2]oct-7-ene-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

(3S,4R,5S)-5-Dimethylaminomethyl-3,4-dihydroxy-cyclohex-1-enecarboxylic acid tert-butyl ester

(R)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-cyclohexa-1,3-dienecarboxylic acid tert-butyl ester

(1S,4S,6R,7S,8R)-7,8-Dihydroxy-2-aza-bicyclo[2.2.2]octane-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

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