6-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate

Base Information

• Chemical Name: 6-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
• CAS No.: 55869-99-3
• Molecular Formula: C17H23NO4
• Molecular Weight: 305.374
• European Community (EC) Number: 637-239-0
• Nikkaji Number: J410.705E
• Wikipedia: Anisodamine
• Wikidata: Q105312733
• Mol file: 55869-99-3.mol

Synonyms:6-hydroxyhyoscyamine;anisodamine;anisodamine hydrobromide;racanisodamine

Chemical Property of 6-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate

Chemical Property:

• Vapor Pressure: 6.49E-08mmHg at 25°C
• Melting Point: 62-63 °C
• Refractive Index: 1.565
• Boiling Point: 423.1 °C at 760 mmHg
• PKA: 14.12±0.10(Predicted)
• Flash Point: 174.8 °C
• PSA: 70.00000
• Density: 1.16g/cm³
• LogP: 0.83960
• Storage Temp.: room temp
• Solubility.: H2O: ≥5mg/mL
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 305.16270821
• Heavy Atom Count: 22
• Complexity: 396

Purity/Quality:

99% ^*data from raw suppliers

Anisodamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CC(CC1C(C2)O)OC(=O)C(CO)C3=CC=CC=C3
• Recent ClinicalTrials: FOLFOX Via HAI Plus Intravenous Irinotecan With or Without Bevacizumab Versus Systemic FOLFOXIRI With or Without Bevacizumab in Initially Unresectable RAS-mutated CRLM Patients
• Uses: 6S-Hydroxyhyoscyamine is a derivative of Hyoscyamine (H674300), a natural compound that has inhibitory activity against cholinesterases.

Technology Process of 6-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate

There total 27 articles about 6-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-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:

scopolamine (51-34-3,138-12-5,64069-63-2,124917-17-5) → (-)-Anisodamine (17659-49-3,32671-33-3,76831-52-2,85760-60-7,126371-43-5,134355-54-7,138876-55-8,55869-99-3) + 7b-Hydroxyhyoscyamine (126371-43-5) + Hyoscyamine (101-31-5)

Guidance literature:

With hydrogen; nickel; In water; at 20 ℃; for 19h;

DOI:10.1016/0031-9422(89)80374-7

Reference yield:

(-)-hyoscyamine hydrobromide (6415-90-3,50700-39-5,306-03-6,4607-53-8) → (-)-Anisodamine (17659-49-3,32671-33-3,76831-52-2,85760-60-7,126371-43-5,134355-54-7,138876-55-8,55869-99-3)

Guidance literature:

With α-ketoglutaric acid; Anisodus tanguticus hyoscyamine 6β-hydroxylase; iron(II) sulfate; In various solvent(s); at 30 ℃; for 2h; pH=7.4; Enzyme kinetics;

DOI:10.1055/s-2005-837825

Reference yield:

(1R,3S,5S)-8-methyl[6β-2H]-8-azabicyclo[3.2.1]octan-3-ol → C17H22(2)HNO4 + (-)-Anisodamine (17659-49-3,32671-33-3,76831-52-2,85760-60-7,126371-43-5,134355-54-7,138876-55-8,55869-99-3)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; camphor-10-sulfonic acid; dicyclohexyl-carbodiimide / dichloromethane / 72 h / 20 °C

2: hydrogenchloride; water / methanol / 20 °C

3: hyoscyamine 6β-hydroxylase; iron(II) sulfate; α-ketoglutaric acid; sodium L-ascorbate / aq. buffer / 0.5 h / 20 °C / pH 6.9 / Enzymatic reaction

With hydrogenchloride; dmap; α-ketoglutaric acid; camphor-10-sulfonic acid; hyoscyamine 6β-hydroxylase; water; iron(II) sulfate; sodium L-ascorbate; dicyclohexyl-carbodiimide; In methanol; dichloromethane;

DOI:10.1021/jacs.8b11585

upstream raw materials:

scopolamine

(-)-hyoscyamine hydrobromide

(2S,3S)-di-4-toluoyltartaric acid

C₁₅H₂₇NO₃Si

Downstream raw materials:

(3R,6R)-tropane-3α,6β-diol

scopolamine

(S)-tropic acid

3α,6β-dihydroxytropane HCl

Refernces

• 1、 Ushimaru, Richiro,Ruszczycky, Mark W.,Liu, Hung-Wen. "Changes in Regioselectivity of H Atom Abstraction during the Hydroxylation and Cyclization Reactions Catalyzed by Hyoscyamine 6β-Hydroxylase". . p. 1062 - 1066. Retrieved 2019/01/23.
• 2、 Li, Jing,Van Belkum, Marco J.,Vederas, John C.. "Functional characterization of recombinant hyoscyamine 6β-hydroxylase from Atropa belladonna". experimental part. p. 4356 - 4363. Retrieved 2012/08/28.