488-06-2

Basic information

• Product Name: LINDELOFIDINE
• Synonyms: LINDELOFIDINE;(1R,7aR)-Hexahydro-1H-pyrrolizine-1-methanol;(1R,7aβ)-Hexahydro-1H-pyrrolizine-1α-methanol
• CAS NO: 488-06-2
• Molecular Formula: C8H15NO
• Molecular Weight: 141.2108
• Mol File: 488-06-2.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: LINDELOFIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: LINDELOFIDINE(488-06-2)
• EPA Substance Registry System: LINDELOFIDINE(488-06-2)

Safety Data

• Hazardous Substances Data: 488-06-2(Hazardous Substances Data)

Upstream product

• 62912-98-5 lindelofidine benzoic acid ester 
• 155140-67-3 7-(hydroxymethyl)tetrahydro-1H-pyrrolizin-3(2H)-one 
• 1036379-56-2 E-thesinine-O-4'-α-rhamnoside 
• 73354-00-4 ethyl (+)-(2R)-2-formyloxy-2,3-dihydro-1H-pyrrolizine-7-carboxylate 
• 78175-08-3 ethyl 6-chloro-8β-pyrrolizidine-1α-carboxylate hydrochloride 
• 73354-01-5 ethyl (+)-2-(R)-2-hydroxy-2,3-dihydro-1H-pyrrolizine-7-carboxylate 
• 73354-03-7 ethyl (+)-6α-hydroxy-8β-pyrrolizidine-1α-carboxylate 
• 73353-98-7 (-)-(2S,4R)-N-formyl-4-formyloxyproline 
• 200397-98-4 (R)-2-[(R)-1-((S)-1-Phenyl-ethyl)-pyrrolidin-2-yl]-pent-4-enoic acid ethyl ester 
• 144688-69-7 tert-butyl 2-methoxypyrrolidine-1-carboxylate 
• 106412-40-2 tert-butyl 2-ethoxypyrrolidine-1-carboxylate 

Relevant articles and documents

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Stereodivergent Synthesis of 1-Hydroxymethylpyrrolizidine Alkaloids

A first stereodivergent strategy for the asymmetric synthesis of all stereoisomers of 1-hydroxymethylpyrrolizidine alkaloids is developed using an asymmetric self-Mannich reaction as a key step. An anti-selective self-Mannich reaction of methyl 4-oxobutanoate with the PMP-amine catalyzed by a chiral secondary amine is successfully optimized for the asymmetric synthesis of (+)-isoretronecanol and (-)-isoretronecanol. A syn-selective self-Mannich reaction catalyzed by proline is utilized for the asymmetric synthesis of the diastereomer, (+)-laburnine, and its enantiomer, (-)-trachelanthamidine.

The stereoselective addition of titanium(IV) enolates of 1,3-oxazolidin-2-one and 1,3-thiazolidine-2-thione to cyclic N-acyliminium ion. The total synthesis of (+)-isoretronecanol

(+)-Isoretronecanol (1) has been prepared in four steps and 36% overall yield via the diastereoselective addition of the titanium(IV) enolate derived from N-4-chlorobutyryl-1,3-thiazolidine-2-thione (3) to N-Boc-2- methoxypyrrolidine (5), which afforded 2-substituted pyrrolidine 7 in 84% yield (8:1 diastereoisomeric ratio), followed by reductive recovery of the chiral auxiliary and cyclization.