3-Azabicyclo[3.3.1]nonane-7-carboxylic acid, 1,5,7-trimethyl-2-oxo-, 3-formylphenyl ester, (1R,5S,7S)-

Base Information

• Chemical Name: 3-Azabicyclo[3.3.1]nonane-7-carboxylic acid, 1,5,7-trimethyl-2-oxo-, 3-formylphenyl ester, (1R,5S,7S)-
• CAS No.: 254440-33-0
• Molecular Formula: C19H23NO4
• Molecular Weight: 329.396

Synonyms:

Chemical Property of 3-Azabicyclo[3.3.1]nonane-7-carboxylic acid, 1,5,7-trimethyl-2-oxo-, 3-formylphenyl ester, (1R,5S,7S)-

Chemical Property:

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Technology Process of 3-Azabicyclo[3.3.1]nonane-7-carboxylic acid, 1,5,7-trimethyl-2-oxo-, 3-formylphenyl ester, (1R,5S,7S)-

There total 7 articles about 3-Azabicyclo[3.3.1]nonane-7-carboxylic acid, 1,5,7-trimethyl-2-oxo-, 3-formylphenyl ester, (1R,5S,7S)- 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: 60.0%

(1R,5S,7S)-1,5,7-Trimethyl-2-oxo-3-aza-bicyclo[3.3.1]nonane-3,7-dicarboxylic acid 7-(3-formyl-phenyl) ester 3-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester → (+)-(1R,5S,7S)-3-aza-2-oxo-1,5,7-trimethylbicyclo[3.3.1]-7-nonanoic acid 3-formylphenyl ester (254440-33-0)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 15h;

DOI:10.1002/1521-3765(20011015)7:20<4512::AID-CHEM4512>3.0.CO;2-H

Reference yield:

(1RS,5SR,7SR)-1,5,7-trimethyl-2-oxo-3-azabicyclo[3.3.1]nonan-7-carboxylic acid methyl ester → (+)-(1R,5S,7S)-3-aza-2-oxo-1,5,7-trimethylbicyclo[3.3.1]-7-nonanoic acid 3-formylphenyl ester (254440-33-0)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. NaOH / dimethylsulfoxide

2: SOCl₂

With sodium hydroxide; thionyl chloride; In dimethyl sulfoxide; 1: Hydrolysis / 2: Chlorination;

DOI:10.1021/ja992209m

Reference yield:

(1RS,5SR,7SR)-1,5,7-trimethyl-2-oxo-3-azabicyclo[3.3.1]nonan-7-carboxylic acid → (+)-(1R,5S,7S)-3-aza-2-oxo-1,5,7-trimethylbicyclo[3.3.1]-7-nonanoic acid 3-formylphenyl ester (254440-33-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: SOCl₂ / 2.5 h / Heating

2.1: 85 mg / Et₃N; DMAP / tetrahydrofuran / 18 h / 20 °C

3.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 23 percent / tetrahydrofuran; hexane / 17 h / -78 - 20 °C

4.1: 60 percent / TFA / 15 h / 20 °C

With dmap; thionyl chloride; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1002/1521-3765(20011015)7:20<4512::AID-CHEM4512>3.0.CO;2-H

upstream raw materials:

meta-hydroxybenzaldehyde

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