233595-58-9

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 2-(1,2-propadienyl)-, 1,1-dimethylethyl ester
• CAS NO: 233595-58-9
• Molecular Formula: C12H19NO2
• Molecular Weight: 209.288
• Mol File: 233595-58-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 2-(1,2-propadienyl)-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 2-(1,2-propadienyl)-, 1,1-dimethylethyl ester(233595-58-9)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 2-(1,2-propadienyl)-, 1,1-dimethylethyl ester(233595-58-9)

Safety Data

• Hazardous Substances Data: 233595-58-9(Hazardous Substances Data)

Upstream product

• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 106-96-7 propargyl bromide 
• 6165-76-0 propargyl p-toluenesulfonate 
• 16156-58-4 prop-2-yn-1-ol methanesulfonate 
• 7138-42-3 2-(hex-1-yn-1-yl)-2-methyloxirane 

Downstream Products

• 51463-41-3 2,3,5,7a-tetrahydro-1H-pyrrolizine 

Relevant articles and documents

Reaction of α-(N-carbamoyl)alkylcuprates with propargyl substrates: Synthetic route to α-amino allenes and Δ3-pyrrolines

(Chemical Equation Presented) Carbamate deprotonation followed by treatment with CuCN·2LiCl affords α-(N-carbamoyl)-alkylcuprates which react with propargyl halides, mesylates, tosylates, phosphates, acetates, and epoxides to give α-(N-carbamoyl) allenes via an anti-SN2′ substitution process. Propargyl halides, sulfonates, and phosphates give good yields of carbamoyl allenes, while the acetates afford low yields. Propargyl substrates undergo regiospecific SN2′ substitution in the absence of severe steric hindrance. The α-(N-carbamoyl) allenes can be cyclized to 2-oxazolidinones or deprotected to afford the free amines which can be cyclized to Δ3-pyrrolines with either AgNO3 or Ru3(CO)12.

Synthesis of amino allenes via reaction of α-aminoalkylcuprates with propargyl substrates

α-Aminoalkylcuprates prepared from carbamates via sequential deprotonation and treatment with CuCN · 2LiCl react with propargyl bromides, mesylates, tosylates, acetates, and epoxides to afford amino allenes via a S(N)2' substitution process. Propargyl bromides and sulfonates give good yields of amino allenes while the acetates afford low yields. Substrates undergo regiospecific S(N)2' substitution and the use Sc(OTf)3 affords improved yields of amino allenes from propargyl epoxides. The Boc protected α-amino allenes can be cyclized to oxazolidones or deprotected to afford the free amines.