(1R,2S,3S,5S)-8-Methyl-3-phenylacetyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid

Base Information

• Chemical Name: (1R,2S,3S,5S)-8-Methyl-3-phenylacetyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid
• CAS No.: 372158-04-8
• Molecular Formula: C₁₇H₂₁NO₃
• Molecular Weight: 287.359
• Mol file: 372158-04-8.mol

Synonyms:

Chemical Property of (1R,2S,3S,5S)-8-Methyl-3-phenylacetyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3S,5S)-8-Methyl-3-phenylacetyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid

There total 9 articles about (1R,2S,3S,5S)-8-Methyl-3-phenylacetyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid 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:

1-((1R,2S,3S,5S)-2-Hydroxymethyl-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-2-phenyl-ethanone (372158-03-7) → (1R,2S,3S,5S)-8-Methyl-3-phenylacetyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid (372158-04-8)

Guidance literature:

1-((1R,2S,3S,5S)-2-Hydroxymethyl-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-2-phenyl-ethanone; With swern reagent;

With sodium chlorite; In 2-methyl-propan-1-ol; water;

DOI:10.1016/S0040-4039(01)01254-0

Reference yield:

benzyllithium (766-04-1) → (1R,2S,3S,5S)-8-Methyl-3-phenylacetyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid (372158-04-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 73 percent / diethyl ether / 3 h

2.1: tBu₄NF / tetrahydrofuran

3.1: Swern reagent

3.2: NaClO₂ / isobutanol; H₂O

With swern reagent; tetra(tert-butyl)-ammonium fluoride; In tetrahydrofuran; diethyl ether; 3.1: Swern oxidation;

DOI:10.1016/S0040-4039(01)01254-0

Reference yield:

(R)-alloecgonine methyl ester (74562-04-2) → (1R,2S,3S,5S)-8-Methyl-3-phenylacetyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid (372158-04-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 87 percent / LiAlH₄ / tetrahydrofuran / 3 h

2.1: 91 percent / imidazole / CH₂Cl₂

3.1: 88 percent / Et₃N / CH₂Cl₂

4.1: 74 percent / ethanol; H₂O / 4 h / Heating

5.1: 83 percent / NaNH₂ / benzene / 24 h / Heating

6.1: 73 percent / diethyl ether / 3 h

7.1: tBu₄NF / tetrahydrofuran

8.1: Swern reagent

8.2: NaClO₂ / isobutanol; H₂O

With 1H-imidazole; lithium aluminium tetrahydride; swern reagent; sodium amide; tetra(tert-butyl)-ammonium fluoride; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; benzene; 8.1: Swern oxidation;

DOI:10.1016/S0040-4039(01)01254-0

upstream raw materials:

1-((1R,2S,3S,5S)-2-Hydroxymethyl-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-2-phenyl-ethanone

benzyllithium

(R)-alloecgonine methyl ester

(1R,2S,3R,5S)-2-Hydroxymethyl-8-methyl-8-aza-bicyclo[3.2.1]octan-3-ol