1013630-68-6

Basic information

• Product Name: (+)-(3R,4S,5R)-3-benzyloxy-4-{[tert-butyl(dimethyl)silyl]oxy}-5-cyano-1-(4-methoxybenzyl)pyrrolidin-2-one
• Synonyms: (+)-(3R,4S,5R)-3-benzyloxy-4-{[tert-butyl(dimethyl)silyl]oxy}-5-cyano-1-(4-methoxybenzyl)pyrrolidin-2-one
• CAS NO: 1013630-68-6
• Molecular Weight: 466.652
• Mol File: 1013630-68-6.mol

Chemical Properties

• CAS DataBase Reference: (+)-(3R,4S,5R)-3-benzyloxy-4-{[tert-butyl(dimethyl)silyl]oxy}-5-cyano-1-(4-methoxybenzyl)pyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(3R,4S,5R)-3-benzyloxy-4-{[tert-butyl(dimethyl)silyl]oxy}-5-cyano-1-(4-methoxybenzyl)pyrrolidin-2-one(1013630-68-6)
• EPA Substance Registry System: (+)-(3R,4S,5R)-3-benzyloxy-4-{[tert-butyl(dimethyl)silyl]oxy}-5-cyano-1-(4-methoxybenzyl)pyrrolidin-2-one(1013630-68-6)

Safety Data

• Hazardous Substances Data: 1013630-68-6(Hazardous Substances Data)

Upstream product

• 1013630-61-9 C₁₉H₁₉NO₄ 
• 56522-24-8 tert-butyldimethylsilyl cyanide 

Relevant articles and documents

Ring expansion versus cyclization in 4-oxoazetidine-2-carbaldehydes catalyzed by molecular iodine: Experimental and theoretical study in concert

Molecular iodine (10 mol%) efficiently catalyzes the ring expansion of 4-oxoazetidine-2-carbaldehydes in the presence of tert-butyldimethylsilyl cyanide, or allylic and propargylic trimethylsilanes to afford protected 5-functionalized-3,4-dihydroxypyrrolidin-2-ones with good yield and high diastereoselectivity, through a C3-C4 bond cleavage of the β-lactam nucleus. Interestingly, in contrast to the iodine-catalyzed reactions of 3-alkoxy-β-lactam aldehydes which lead to the corresponding γ-lactam derivatives (rearrangement adducts), the reactions of 3 aryloxy-β-lactam aldehydes under similar conditions gave β-lactam-fused chromanes (cyclization adducts) as the sole products, through exclusive electrophilic aromatic substitution involving the C3 aromatic ring and the carbaldehyde. In order to support the mechanistic proposals, theoretical studies have been performed.

I2-Catalyzed enantioselective ring expansion of β-lactams to γ-lactams through a novel C3-C4 bond cleavage. Direct entry to protected 3,4-dihydroxypyrrolidin-2-one derivatives

Molecular iodine (10 mol%) efficiently catalyzes the ring expansion of 4-oxoazetidine-2-carbaldehydes 1 in the presence of tert-butyldimethyl cyanide to afford protected 5-cyano-3,4-dihydroxypyrrolidin-2-ones 2 with good yield and high diastereoselectivity, through a novel C3-C4 bond cleavage of the β-lactam nucleus. The Royal Society of Chemistry.

Direct synthesis of protected enantiopure 5-cyano-3,4-dihydroxypyrrolidin- 2-ones from β-lactam aldehydes catalyzed by iodine

A single-step catalytic ring-expansion approach from 4-oxoazetidine-2- carbaldehydes to protected enantiopure 5-cyano-3,4-dihydroxypyrrolidin-2-ones has been achieved by the use of the commercially available and inexpensive reagent, molecular iodine, in the presence of tert-butyldimethyl cyanide. Interestingly, the catalyst directs the reaction toward the selective rearrangement reaction of the β-lactam nucleus rather than cyanohydrin formation. Georg Thieme Verlag Stuttgart.