399044-21-4

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 2-(2-propenyl)-, 1,1-dimethylethyl ester, (2S)-
• CAS NO: 399044-21-4
• Molecular Formula: C12H21NO2
• Molecular Weight: 211.304
• Mol File: 399044-21-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 2-(2-propenyl)-, 1,1-dimethylethyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 2-(2-propenyl)-, 1,1-dimethylethyl ester, (2S)-(399044-21-4)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 2-(2-propenyl)-, 1,1-dimethylethyl ester, (2S)-(399044-21-4)

Safety Data

• Hazardous Substances Data: 399044-21-4(Hazardous Substances Data)

Upstream product

• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 106-95-6 allyl bromide 
• 19206-69-0 allyl diphenyl phosphate 

Downstream Products

• 197229-64-4 (S)-benzyl 2-allylpyrrolidine-1-carboxylate 
• 399044-23-6 (S)-Δ^6,7-indolizidin-5-one 

Relevant articles and documents

Asymmetric lithiation trapping of N -boc heterocycles at temperatures above -78°C

The asymmetric lithiation trapping of N-Boc heterocycles using s-BuLi/chiral diamines at temperatures up to -20°C is reported. Depending on the N-Boc heterocycle, lithiation is accomplished using s-BuLi and (-)-sparteine or the (+)-sparteine surrogate in the temperature range -50 to -20°C for short reaction times (2-20 min). Subsequent electrophilic trapping or transmetalation-Negishi coupling delivered functionalized N-Boc heterocycles in 47-95% yield and 77:23-93:7 er. With N-Boc pyrrolidine, trapped products can be generated in ～90:10 er even at -20°C.

Regio- and enantioselective control in the reactions of α-(N-Carbamoyl)alkylcuprates with allylic phosphates

α-(N-Carbamoyl)alkylcuprates (RCuCNLi or R2CuLi) react with allylic phosphates to afford homoallylic amines in good chemical yields. Regioselectivity is governed by steric factors in both the cuprate reagent and phosphate substrate and systems can be designed to give either the S N2′ or SN2 substitution product cleanly. Excellent enantioselectivities can be achieved with either a scalemic α-di[(N- carbamoyl)-alkyl]cuprate and an achiral phosphate or with a scalemic allylic phosphate and an achiral cuprate reagent.