(3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one;hydron;chloride

Base Information

• Chemical Name: (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one;hydron;chloride
• CAS No.: 54-71-7
• Molecular Formula: C11H16N2O2^.HCl
• Molecular Weight: 244.721
• Hs Code.: 29399990
• Mol file: 54-71-7.mol

Synonyms:Salagen;Sanpilo;Epicar;Isopto carpine;pilocarpinium chloride;C11H16N2O2.ClH;Pilocarpine monohydrochloride (8CI);2 (3H)-furanona, 3-etildihidro-4-[(1-metil-1H-imidazol-5-il) metil]-, clorhidrato (1:1), (3S, 4R)-;2 (3H)-furanona, 3-etildihidro-4-[(1-metil-1H-imidazol-5-il) metil]-, triptamina, (3S, 4R)-;2 (3H)-furanona, 3-etildihidro-4-[(1-metil-1H-imidazol-5-il) metil]-, triptamina,(3S-cis)-;2(3H)-Furanone 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-monohydrochloride (3S-cis)-;2(3H)-Furanone 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-monohydrochloride (3S4R)-(9CI)

Chemical Property of (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one;hydron;chloride

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 1.16E-07mmHg at 25°C
• Melting Point: 199-204 °C
• Refractive Index: 1.584
• Boiling Point: 431.8 °C at 760 mmHg
• Flash Point: 215 °C
• PSA: 44.12000
• Density: 1.22 g/cm³
• LogP: 1.96380
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: H2O: 100 mg/mL
• Water Solubility.: soluble
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 244.0978555
• Heavy Atom Count: 16
• Complexity: 245

Purity/Quality:

98% min, ^*data from raw suppliers

Pilocarpine hydrochloride ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+,T
• Statements: 26/28-25-23
• Safety Statements: 25-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [H+].CCC1C(COC1=O)CC2=CN=CN2C.[Cl-]
• Isomeric SMILES: [H+].CC[C@H]1[C@H](COC1=O)CC2=CN=CN2C.[Cl-]
• Description: It is a bioactive chemical usually used as pharmaceutical agents such as acetylcholine receptor agonist, antiglaucoma agent, moitic, and sialogogue. Specifically, due to its desirable activity as acetylcholine receptor agonist, this chemical has been introduced to regulate muscarinic acetylcholine receptor function in acetylcholinesterase knockout mice.1 Moreover, because of its good antiglaucoma effect, this substance is applied in a timolol plus maximum-tolerated antiglaucoma therapy.2 In addition, this chemical has been demonstrated to show a favourable miotic activity when incorporated into polymer capsules.3 Besides, this compound can be utilized to relieve the xerostomia due to chronic graft-versus-host disease or total-body irradiation after bone-marrow transplantation for hematologic malignancies.4
• Uses: Antiglaucoma agent; miotic; sialogogue. Acetylcholine receptor agonist (+)-Pilocarpine hydrochloride is a muscarinic M1 and M2 acetylcholine receptor agonist with pKB values of 5 and 3.7, respectively. Systemic administration of (+)-Pilocarpine hydrochloride is typically used as an animal model for temporal lobe epilepsy and can mimic the generation of complex partial seizures by producing changes in hippocampal neuron morphology, membrane properties, and synaptic responses.
• Therapeutic Function: Cholinergic
• Clinical Use: Pilocarpine, the salt of an alkaloid obtained from Pilocarpus jaborandi, is an example of a muscarinic agonist that does not adhere to the traditional SAR. In 1876, Langley reported that extracts containing the alkaloid stimulated the end organs of parasympathetic neurons. The structure of pilocarpine was reported in 1901. Pilocarpine is marketed as tablets (Salogen), an ophthalmic solution, and gel. It penetrates the eye well and is the miotic of choice for open-angle glaucoma and to terminate acute angle closure attacks. It also is used for the treatment of xerostomia (dryness of the mouth) caused by radiation therapy of the head and neck, Sjogren's syndrome, or as a side effect of some psychotropic drugs.

Technology Process of (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one;hydron;chloride

There total 6 articles about (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one;hydron;chloride 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:

(2S,3R)-2-ethyl-3-(methoxycarbonyl)4-(1-methylimidazol-5-yl)-butyricacid → pilocarpine hydrochloride (54-71-7)

Guidance literature:

With lithium borohydride; sodium hydrogencarbonate; In hydrogenchloride; methanol; water; isopropyl alcohol;

Reference yield:

(3S,4RS,5RS)-3-ethyl-4-(methoxycarbonyl)-5-(1-methyl-1H-imidazol-5-yl)dihydro-2(3H)-furanone → pilocarpine hydrochloride (54-71-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / Pd/C (5percent) / methanol / 60 h / 3102.9 Torr

2: 1.) NaBH₄, 2.) conc. aq. HCl / 1a.) iPrOH, -5 deg C, 1 h, 1b.) RT, 21 h, 2.) MeOH, water, 2 h

With hydrogenchloride; sodium tetrahydroborate; hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jo00057a031

Reference yield:

(R)-3-ethylidene-4-[(1-methylimidazol-5-yl)methyl]tetrahydrofuran-2-one (1192231-13-2) → pilocarpine hydrochloride (54-71-7)

Guidance literature:

(R)-3-ethylidene-4-[(1-methylimidazol-5-yl)methyl]tetrahydrofuran-2-one; With platinum(IV) oxide; hydrogen; In methanol; at 20 ℃; for 24h;

With hydrogenchloride; In ethanol; water; at 0 ℃; Cooling;

DOI:10.1016/j.tet.2009.07.010

upstream raw materials:

(R)-3-ethylidene-4-[(1-methylimidazol-5-yl)methyl]tetrahydrofuran-2-one

Downstream raw materials:

C₁₁H₁₆N₂O₂*ClH*C₆H₂Cl₂O₄

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid 4-tert-butyl-benzyl ester

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid 4-chloro-benzyl ester

(2S,3R)-2-Ethyl-3-hydroxymethyl-4-(3-methyl-3H-imidazol-4-yl)-butyric acid 2-methyl-benzyl ester

Refernces

• 1、 Davies, Stephen G.,Roberts, Paul M.,Stephenson, Peter T.,Storr, Helen R.,Thomson, James E.. "A practical and scaleable total synthesis of the jaborandi alkaloid (+)-pilocarpine". experimental part. p. 8283 - 8296. Retrieved 2009/12/28.
• 2、 Dener, Jeffrey M.,Zhang, Lin-Hua,Rapoport, Henry. "An Effective Chirospecific Synthesis of (+)-Pilocarpine from L-Aspartic Acid". . p. 1159 - 1166. Retrieved 2007/10/02.