203866-18-6

Basic information

• Product Name: BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER
• Synonyms: BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER;METHYL N-(TERT-BUTOXYCARBONYL)-(2S, 4R)-4-FLUOROPROLINATE;N-T-BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER;(4R)-1-BOC-4-FLUORO-L-PROLINE METHYL ESTER;N-Boc-trans-4-fluoro-L-proline methyl ester;1-tert-Butyl 2-methyl (2S,4R)-4-fluoro-1,2-pyrrolidinedicarboxylate;(2S,4R)-4-Fluoro-1,2-pyrrolidinedicarboxylic acid 1-(tert-butyl) 2-methyl ester;(2S,4R)-1-tert-Butyl 2-Methyl 4-fluoropyrrolidine-1,2-dicarboxylate
• CAS NO: 203866-18-6
• Molecular Formula: C₁₁H₁₈FNO₄
• Molecular Weight: 247.26
• Product Categories: Asymmetric Synthesis;Building Blocks;Chemical Synthesis;Chiral Building Blocks;Fluorinated Building Blocks;Heterocyclic Building Blocks;Heterocyclic Fluorinated Building Blocks;Other Fluorinated Heterocycles;Pyrrolidines
• Mol File: 203866-18-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 36-39°C
• Boiling Point: 296.525 °C at 760 mmHg
• Flash Point: 110 °C
• Appearance: /
• Density: 1.16
• Vapor Pressure: 0.00143mmHg at 25°C
• Refractive Index: 1.465
• Storage Temp.: 2-8°C
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER(203866-18-6)
• EPA Substance Registry System: BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER(203866-18-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 203866-18-6(Hazardous Substances Data)

Usage

Uses

N-Boc-trans-4-fluoro-L-proline methyl ester is used to prepare (S)-2-[N-(N'-benzyl-(S)-4-fluoro-L-prolyl)amino]benzophenone by reacting with of 2-aminobenzophenone in the presence of potassium tert -butoxide.

InChI:InChI=1/C11H18FNO4/c1-11(2,3)17-10(15)13-6-7(12)5-8(13)9(14)16-4/h7-8H,5-6H2,1-4H3/t7-,8+/m1/s1

Upstream product

• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 

Downstream Products

• 1138324-48-7 (2S,4R)-tert-butyl 4-fluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 2097518-76-6 (2R,7aS)-(2-fluorohexahydro-1H-pyrrolizin-7a-yl)methanol 
• 2097518-76-6 ((2R,7aR)-2-fluorotetrahydro-1H-pyrrolizin-7a(5H)-yl)methanol 
• 2097518-76-6 ((2R)-2-fluorotetrahydro-1H-pyrrolizin-7a(5H)-yl)methanol 
• 237076-75-4 (2S,4R)-4-fluoro-5-oxo-pyrrolidine-2-carboxylic acid 
• 393810-25-8 (2S,4R)-4-fluoro-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 60604-36-6 (2S,4R)-4-fluoropyrrolidine-2-carboxylic acid hydrochloride 

Relevant articles and documents

Photoredox-catalyzed deoxyfluorination of activated alcohols with Selectfluor

Herein we disclose a deoxyfluorination of alcohols with an electrophilic fluorine source via visible-light photoredox catalysis. This radical-mediated C–F coupling is capable of fluorinating secondary and tertiary alcohols efficiently, complementing previously reported nucleophilic deoxyfluorination protocols.

Practical synthesis of Boc and Fmoc protected 4-fluoro and 4-difluoroprolines from trans-4-hydroxyproline

Boc-cis-4-fluoro-L-proline and 4-difluoro-L-proline, usable in classical peptide synthesis, were obtained in respectively 71% (3 steps) and 65% (4 steps) overall yields from the readily available trans-4-hydroxy-L-proline methyl ester. The corresponding fluorinated trans-isomer was isolated in 24% yield (5 steps). Transformation of Boc-protected compounds to their Fmoc-equivalents was performed in high yields.