183433-65-0

Basic information

• Product Name: 3-Pyridinecarboxaldehyde, 6-chloro-4-(2-ethyl-1,3-dioxolan-2-yl)-2-methoxy-
• CAS NO: 183433-65-0
• Molecular Formula: C12H14ClNO4
• Molecular Weight: 271.7
• Mol File: 183433-65-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-Pyridinecarboxaldehyde, 6-chloro-4-(2-ethyl-1,3-dioxolan-2-yl)-2-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinecarboxaldehyde, 6-chloro-4-(2-ethyl-1,3-dioxolan-2-yl)-2-methoxy-(183433-65-0)
• EPA Substance Registry System: 3-Pyridinecarboxaldehyde, 6-chloro-4-(2-ethyl-1,3-dioxolan-2-yl)-2-methoxy-(183433-65-0)

Safety Data

• Hazardous Substances Data: 183433-65-0(Hazardous Substances Data)

Upstream product

• 183433-63-8 2,6-dichloro-4-(2-ethyl-1,3-dioxolan-2-yl)pyridine 
• 68-12-2 N,N-dimethyl-formamide 
• 183433-64-9 6-chloro-4-(2-ethyl-1,3-dioxolan-2-yl)-2-methoxypyridine 
• 2591-86-8 N-Formylpiperidine 
• 183433-62-7 1-(2,6-dichloropyridin-4-yl)propan-1-one 
• 5398-44-7 2,6-dichloropyridine-4-carboxylic acid 
• 99-11-6 citrazinic acid 

Downstream Products

• 185135-84-6 4-((R)-1-Acetoxymethyl-1-hydroxy-propyl)-5-benzyloxymethyl-6-methoxy-pyridine-2-carboxylic acid propyl ester 
• 183433-68-3 5-Benzyloxymethyl-4-(2-ethyl-[1,3]dioxolan-2-yl)-6-methoxy-pyridine-2-carboxylic acid propyl ester 
• 183433-96-7 5-Benzyloxymethyl-4-((S)-1-formyl-1-hydroxy-propyl)-6-methoxy-pyridine-2-carboxylic acid propyl ester 
• 183433-70-7 5-Benzyloxymethyl-6-methoxy-4-propionyl-pyridine-2-carboxylic acid propyl ester 
• 183433-72-9 5-Benzyloxymethyl-6-methoxy-4-(1-methylene-propyl)-pyridine-2-carboxylic acid propyl ester 
• 183433-67-2 3-Benzyloxymethyl-6-chloro-4-(2-ethyl-[1,3]dioxolan-2-yl)-2-methoxy-pyridine 
• 183434-02-8 propyl (S)-4-ethyl-3,4,7,8-tetrahydro-4-hydroxy-3,8-dioxo-1H-pyrano[3,4-c] pyridine-6-carboxylate 
• 183433-75-2 5-Benzyloxymethyl-4-((S)-1-hydroxy-1-hydroxymethyl-propyl)-6-methoxy-pyridine-2-carboxylic acid propyl ester 
• 183433-74-1 5-Benzyloxymethyl-4-(1-hydroxy-1-hydroxymethyl-propyl)-6-methoxy-pyridine-2-carboxylic acid propyl ester 
• 97682-44-5 irinotecan 
• 86639-52-3 7-ethyl-10-hydroxycamptothecin 
• 110351-94-5 (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione 
• 183433-64-9 6-chloro-4-(2-ethyl-1,3-dioxolan-2-yl)-2-methoxypyridine 
• 183433-66-1 [6-Chloro-4-(2-ethyl-[1,3]dioxolan-2-yl)-2-methoxy-pyridin-3-yl]-methanol 

Relevant articles and documents

Practical asymmetric synthesis of (S)-4,ethyl-7,8-dihydro-4-hydroxy-1H- pyrano[3,4-f]indolizine-3,6,10(4H)-trione, a key intermediate for the synthesis of Irinotecan and other camptothecin analogs

A practical asymmetric synthesis of (S) 4-ethyl-7,8-dihydro-4-hydroxy- 1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione (1), a versatile intermediate for the synthesis of camptothecin analogs, was developed. Commercially available citrazinic acid is converted in four steps into the 2-chloro-6- methoxypyridine 5. An ortho-directed metalation followed by reaction with a formamide produces an aldehyde with the required 2,3,4,6-substituted pyridine (6) with high regioselectivity. After refunctionalization of the aldehyde, the chloropyridine is converted into an ester by a facile palladium-mediated carbonylation reaction. Wittig reaction and racemic osmylation produce the diol 16 which is resolved by an efficient lipase resolution to an ee > 99%, and a one-pot recycle of the unwanted diol enantiomer was developed. A series of high-yielding oxidation and deprotection steps convert (S)-16 into the pyridone 25, which is then converted into 1 with an ee > 99.6%.