64168-68-9

Basic information

• Product Name: Spiro[1-azabicyclo[2.2.2]octane-3,2'-oxirane] hydrochloride
• Synonyms: SPIRO[1-AZABICYCLO[2.2.2]OCTANE-3,2''-OXIRANE],HYDROCHLORIDE(9CI);Spiro[1-azabicyclo[2.2.2]octane-3,2'-oxirane] hydrochloride;Spiro[1-azabicyclo[2.2.2]octane-3,2'-oxirane] HCl;2'-oxirane];Spiro[1-azabicyclo[2.2.2]octane-3;Spiro[1-azabicyclo[2.2.2]octane-3,2'-oxirane],hydrochloride (1:1);1'-Azaspiro[oxirane-2,3'-bicyclo[2.2.2]octane] hydrochloride
• CAS NO: 64168-68-9
• Molecular Formula: C₈H₁₃NO*ClH
• Molecular Weight: 175.66
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 64168-68-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 250.7 °C at 760 mmHg
• Flash Point: 105.4 °C
• Appearance: /
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Spiro[1-azabicyclo[2.2.2]octane-3,2'-oxirane] hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Spiro[1-azabicyclo[2.2.2]octane-3,2'-oxirane] hydrochloride(64168-68-9)
• EPA Substance Registry System: Spiro[1-azabicyclo[2.2.2]octane-3,2'-oxirane] hydrochloride(64168-68-9)

Safety Data

• Hazardous Substances Data: 64168-68-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Synthetic route

trimethylsulfoxonium iodide (1774-47-6) + 3-quinuclidinone hydrochloride (1193-65-3) → Spiro- Hydrochlorid (64168-68-9)

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In dimethyl sulfoxide at 25 - 30℃; for 0.5h; Inert atmosphere; Stage #2: 3-quinuclidinone hydrochloride In dimethyl sulfoxide at 25℃; for 8h; Inert atmosphere;	70%

Spiro- Hydrochlorid (64168-68-9) → 3-hydroxy-3-(mercaptomethyl)quinuclidine (107220-26-8)

Conditions	Yield
With hydrogen sulfide; sodium hydroxide In water at 45℃; for 2.5h;	50%

Spiro- Hydrochlorid (64168-68-9) → trans-cevimeline + cevimeline

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen sulfide; sodium hydroxide / water / 2.5 h / 45 °C 2: toluene-4-sulfonic acid / isopropyl alcohol / 3 h / 70 °C View Scheme

Spiro- Hydrochlorid (64168-68-9) → 2-methylspiro (1,3-oxathiolane-5,3')quinuclidine hydrochloride (173553-37-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen sulfide; sodium hydroxide / water / 2.5 h / 45 °C 2: boron trifluoride diethyl etherate / dichloromethane View Scheme

Upstream product

• 1774-47-6 trimethylsulfoxonium iodide 
• 1193-65-3 3-quinuclidinone hydrochloride 

Downstream Products

• 107220-27-9 trans-cevimeline 
• 107220-27-9 cevimeline 
• 107220-26-8 3-hydroxy-3-(mercaptomethyl)quinuclidine 
• 173553-37-2 Cevimeline hydrochloride 

Relevant articles and documents

A new route to cevimeline

The present work demonstrates a new route for the synthesis of cevimeline in which safe and odorless thiourea is utilized as a thiolating reagent.