(1S,6S,7S)-9-Aza-bicyclo[4.2.1]nona-2,4-diene-7,9-dicarboxylic acid 9-methyl ester 7-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester

Base Information

• Chemical Name: (1S,6S,7S)-9-Aza-bicyclo[4.2.1]nona-2,4-diene-7,9-dicarboxylic acid 9-methyl ester 7-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester
• CAS No.: 171367-06-9
• Molecular Formula: C₂₇H₃₅NO₄
• Molecular Weight: 437.579
• Mol file: 171367-06-9.mol

Synonyms:

Chemical Property of (1S,6S,7S)-9-Aza-bicyclo[4.2.1]nona-2,4-diene-7,9-dicarboxylic acid 9-methyl ester 7-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,6S,7S)-9-Aza-bicyclo[4.2.1]nona-2,4-diene-7,9-dicarboxylic acid 9-methyl ester 7-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester

There total 1 articles about (1S,6S,7S)-9-Aza-bicyclo[4.2.1]nona-2,4-diene-7,9-dicarboxylic acid 9-methyl ester 7-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] 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: 15.0%

(-)-8-phenylmenthyl acrylate (72526-00-2) → (1S,6S,7S)-9-Aza-bicyclo[4.2.1]nona-2,4-diene-7,9-dicarboxylic acid 9-methyl ester 7-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester (171367-06-9) + (1R,6R,7S)-9-Aza-bicyclo[4.2.1]nona-2,4-diene-7,9-dicarboxylic acid 9-methyl ester 7-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester (171485-27-1)

Guidance literature:

Irradiation;

DOI:10.1021/jo00128a007

Reference yield: 85.0%

methanol (67-56-1) + (1S,6S,7S)-9-Aza-bicyclo[4.2.1]nona-2,4-diene-7,9-dicarboxylic acid 9-methyl ester 7-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester (171367-06-9) → (1S,2R,5S,6S)-2-Dimethoxymethyl-8-aza-bicyclo[3.2.1]oct-3-ene-6,8-dicarboxylic acid 8-methyl ester 6-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester (171367-08-1)

Guidance literature:

With thallium(III) nitrate;

DOI:10.1021/jo00128a007

Reference yield:

(1S,6S,7S)-9-Aza-bicyclo[4.2.1]nona-2,4-diene-7,9-dicarboxylic acid 9-methyl ester 7-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester (171367-06-9) → (+)-ferruginine

Guidance literature:

Multi-step reaction with 9 steps

1: 85 percent / Tl(NO₃)3*3H₂O

2: 84 percent / aq. LiOH / methanol

3: N-methylmorpholine

4: Et₃N

5: t-BuSH / Irradiation

6: aq. TFA / acetone

7: diethyl ether

8: LiAlH₄ / diethyl ether

9: Dess-Martin periodinane / CH₂Cl₂

With 4-methyl-morpholine; lithium hydroxide; lithium aluminium tetrahydride; Dess-Martin periodane; 2-methylpropan-2-thiol; triethylamine; trifluoroacetic acid; thallium(III) nitrate; In methanol; diethyl ether; dichloromethane; acetone;

DOI:10.1021/jo00128a007

upstream raw materials:

(-)-8-phenylmenthyl acrylate

Downstream raw materials:

(1S,2R,5S,6S)-2-Dimethoxymethyl-8-aza-bicyclo[3.2.1]oct-3-ene-6,8-dicarboxylic acid 8-methyl ester 6-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester