(1R,2S,3S,5S)-3-(3,4-Dichloro-phenyl)-8-prop-2-ynyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (1R,2S,3S,5S)-3-(3,4-Dichloro-phenyl)-8-prop-2-ynyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester
• CAS No.: 196295-98-4
• Molecular Formula: C₁₈H₁₉Cl₂NO₂
• Molecular Weight: 352.26
• Mol file: 196295-98-4.mol

Synonyms:(1R,2S,3S,5S)-3-(3,4-Dichloro-phenyl)-8-prop-2-ynyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester

Chemical Property of (1R,2S,3S,5S)-3-(3,4-Dichloro-phenyl)-8-prop-2-ynyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3S,5S)-3-(3,4-Dichloro-phenyl)-8-prop-2-ynyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester

There total 5 articles about (1R,2S,3S,5S)-3-(3,4-Dichloro-phenyl)-8-prop-2-ynyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl 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: 78.0%

propargyl bromide (106-96-7) + O-456 (146725-34-0) → (1R,2S,3S,5S)-3-(3,4-Dichloro-phenyl)-8-prop-2-ynyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester (196295-98-4)

Guidance literature:

With potassium iodide; In ethanol; toluene; Heating;

DOI:10.1002/(SICI)1099-1344(199709)39:9<757::AID-JLCR24>3.0.CO;2-J

Reference yield:

3,4-dichlorophenylmagnesium bromide (79175-35-2) → (1R,2S,3S,5S)-3-(3,4-Dichloro-phenyl)-8-prop-2-ynyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester (196295-98-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.) trifluoroacetic acid / 1.) Et₂O, -40 deg C, 3 h, 2.) Et₂O, -78 deg C, 1 h

2: 1.25 h / 120 °C

3: AcOH, Zn / 24 h / Ambient temperature

4: 78 percent / KI / ethanol; toluene / Heating

With acetic acid; trifluoroacetic acid; potassium iodide; zinc; In ethanol; toluene;

DOI:10.1002/(SICI)1099-1344(199709)39:9<757::AID-JLCR24>3.0.CO;2-J

Reference yield:

(-)-cocaine hydrochloride (53-21-4) → (1R,2S,3S,5S)-3-(3,4-Dichloro-phenyl)-8-prop-2-ynyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester (196295-98-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 0.75 N aq. HCl / 3 h / Heating

2: POCl₃ / Heating

3: 168 h / Ambient temperature

4: 2.) trifluoroacetic acid / 1.) Et₂O, -40 deg C, 3 h, 2.) Et₂O, -78 deg C, 1 h

5: 1.25 h / 120 °C

6: AcOH, Zn / 24 h / Ambient temperature

7: 78 percent / KI / ethanol; toluene / Heating

With hydrogenchloride; acetic acid; trifluoroacetic acid; potassium iodide; zinc; trichlorophosphate; In ethanol; toluene;

DOI:10.1002/(SICI)1099-1344(199709)39:9<757::AID-JLCR24>3.0.CO;2-J

upstream raw materials:

propargyl bromide

O-456

3,4-dichlorophenylmagnesium bromide

(-)-cocaine hydrochloride

Downstream raw materials:

(1R,2S,3S,5S)-3-(3,4-Dichloro-phenyl)-8-((E)-3-tributylstannanyl-allyl)-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester