(S)-(1R,3s,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl 3-hydroxy-2-phenylpropanoate

Base Information

• Chemical Name: (S)-(1R,3s,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl 3-hydroxy-2-phenylpropanoate
• CAS No.: 61616-97-5
• Molecular Formula: C₁₇H₂₁NO₃
• Molecular Weight: 287.359
• Mol file: 61616-97-5.mol

Synonyms:

Chemical Property of (S)-(1R,3s,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl 3-hydroxy-2-phenylpropanoate

Chemical Property:

• Boiling Point: 430.2±45.0 °C(Predicted)
• PKA: 14.11±0.10(Predicted)
• Density: 1.21±0.1 g/cm3(Predicted)

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 6,7-Dehydrohyoscyamine is a derivative of Scopolamine (S200000), an acetylcholine antagonist. Used in treatment of motion sickness; antiemetic; antispasmodic; mydriatic; preanesthetic medicant.

Technology Process of (S)-(1R,3s,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl 3-hydroxy-2-phenylpropanoate

There total 8 articles about (S)-(1R,3s,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl 3-hydroxy-2-phenylpropanoate 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: 96.0%

scopolamine (51-34-3,138-12-5,64069-63-2,124917-17-5) → (αS)-α-(hydroxymethyl)benzeneacetic acid (endo)-8-methyl8-azabicyclo[3.2.1]oct-6-en-3-yl ester (22150-33-0,54725-48-3,61616-97-5)

Guidance literature:

With ethanol; copper; zinc;

DOI:10.1016/j.bmcl.2003.09.081

Reference yield: 88.0%

scopolamine hydrobromide trihydrate (152612-85-6) → (αS)-α-(hydroxymethyl)benzeneacetic acid (endo)-8-methyl8-azabicyclo[3.2.1]oct-6-en-3-yl ester (22150-33-0,54725-48-3,61616-97-5)

Guidance literature:

With zinc/copper couple; In ethanol; for 16h; Reflux;

Reference yield: 85.0%

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol (20513-09-1) + (αS)-α-(acetoxymethyl)benzeneacetyl chloride (183626-74-6) → (αS)-α-(hydroxymethyl)benzeneacetic acid (endo)-8-methyl8-azabicyclo[3.2.1]oct-6-en-3-yl ester (22150-33-0,54725-48-3,61616-97-5)

Guidance literature:

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol; With toluene-4-sulfonic acid; In diethyl ether; at 20 ℃; for 0.666667h;

(αS)-α-(acetoxymethyl)benzeneacetyl chloride; In benzene; at 82 ℃; for 2.5h;

With hydrogenchloride; In benzene; at 20 ℃; for 12h;

DOI:10.1002/hlca.200390258

upstream raw materials:

trop-6-ene-3endo-ol; hydrochloride

scopolamine

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol

(αS)-α-(acetoxymethyl)benzeneacetyl chloride

Downstream raw materials:

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol

scopolamine