540501-37-9

Basic information

• Product Name: (S)-2-Hydroxymethyl-4-[1-phenyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid tert-butyl ester
• Synonyms: (S)-2-Hydroxymethyl-4-[1-phenyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS NO: 540501-37-9
• Molecular Weight: 289.375
• Mol File: 540501-37-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-2-Hydroxymethyl-4-[1-phenyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Hydroxymethyl-4-[1-phenyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid tert-butyl ester(540501-37-9)
• EPA Substance Registry System: (S)-2-Hydroxymethyl-4-[1-phenyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid tert-butyl ester(540501-37-9)

Safety Data

• Hazardous Substances Data: 540501-37-9(Hazardous Substances Data)

Upstream product

• 540501-26-6 (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenyl)methylenepyrrolidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 61478-26-0 tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 125653-58-9 (2S,4R)-2-(tert-butyldimethylsilanyloxymethyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 220993-22-6 (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-oxopyrrolidine-1-carboxylate 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 153074-95-4 (2S,4R)-4-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 

Relevant articles and documents

Asymmetric hydrogenations for the synthesis of boc-protected 4-alkylprolinols and prolines

The utility of 4-substituted prolinols and their corresponding prolines in peptides, peptidomimetics, and natural products has motivated researchers to find new and efficient routes for their preparation. Herein, we report a general approach to the synthesis of Boc-protected 4-alkylprolinols and prolines via a divergent asymmetric hydrogenation strategy. Intermediate exocyclic olefins were prepared by Wittig-type reactions with ketone 6 and subjected to hydroxyl and sterically directed reductions. The Crabtree catalyst (Ir[COD] PyPCy3PF6) proved to be highly effective in diastereoselective hydrogenations to give trans- substituted pyrrolidines (9). Good facial selectivities were also observed in heterogeneous hydrogenations with Raney-nickel to obtain cis-substituted pyrrolidines (11). Employing this strategy, we describe the synthesis of novel prolinol and proline-based building blocks for incorporation into biologically relevant peptidomimetics.