73323-65-6

Basic information

• Product Name: BOC-D-PRO-OME
• Synonyms: BOC-D-PROLINE METHYL ESTER;BOC-D-PRO-OME;BOC-D-PYRD(2)-OME;R-1-BOC-PYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER;N-ALPHA-T-BUTOXYCARBONYL-D-PROLINE METHYL ESTER;N-ALPHA-T-BUTOXYCARBONYL-D-PYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER;BOC-D-PROLINE METHYLESTER LIQUID;N-BOC-D-PROLINE METHYL ESTER
• CAS NO: 73323-65-6
• Molecular Formula: C₁₁H₁₉NO₄
• Molecular Weight: 229.27
• EINECS: 233-720-0
• Product Categories: Pyrrole&Pyrrolidine&Pyrroline
• Mol File: 73323-65-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 288.6 °C at 760 mmHg
• Flash Point: 128.3 °C
• Appearance: /
• Density: 1.12 g/cm³
• Vapor Pressure: 0.00232mmHg at 25°C
• Refractive Index: 1.4510-1.4550
• Storage Temp.: Store at 0-5°C
• Solubility: Soluble in DMSO.
• PKA: -3.35±0.40(Predicted)
• CAS DataBase Reference: BOC-D-PRO-OME(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-PRO-OME(73323-65-6)
• EPA Substance Registry System: BOC-D-PRO-OME(73323-65-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 73323-65-6(Hazardous Substances Data)

Usage

Uses

N-Boc-D-proline methyl ester is an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff fields.

InChI:InChI=1/C11H19NO4/c1-11(2,3)16-10(14)12-7-5-6-8(12)9(13)15-4/h8H,5-7H2,1-4H3/t8-/m1/s1

Upstream product

• 145681-01-2 (+/-)-N-tert-butoxycarbonylproline methyl ester 
• 294659-30-6 methyl 1-(tert-butyloxycarbonyl)pyrrole-2-carboxylate 

Downstream Products

• 59378-81-3 1-(tert-butoxycarbonyl)prolin-2R-ol 
• 347188-97-0 (2R,5R)-5-[(S)-methoxycarbonyl(4-bromophenyl)methyl]proline methylester 
• 22348-32-9 (R)-α,α-diphenylprolinol 
• 833473-71-5 C₃₀H₂₈ClFN₄O₃S 
• 833473-70-4 (R)-N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(pyrrolidin-2-ylethynyl)thieno[3,2-d]pyrimidin-4-amine 
• 871716-67-5 (R)-N-(tert-butoxycarbonyl)-2-(2-chloroacetyl)pyrrolidine 
• 924907-34-6 (R)-2-(2-chlorophenoxymethyl)pyrrolidine 
• 1201581-68-1 4-[(R)-2-(2-chlorophenoxymethyl)pyrrolidin-1-yl]-1H-pyrazolo[3,4-d]pyrimidine 
• 1201581-67-0 7-[(R)-2-(2-chlorophenoxymethyl)pyrrolidin-1-yl]-3H-imidazo[4,5-b]pyridine 
• 924907-14-2 6-[(R)-2-(2-chlorophenoxymethyl)-pyrrolidin-1-yl]-9H-purine 
• 1310416-89-7 C₁₈H₂₂FN₃O₂S 
• 871716-68-6 C₁₂H₁₉N₃O₂S 
• 1310416-99-9 C₁₃H₁₄FN₃S 

Relevant articles and documents

Catalytic Asymmetric Hydrogenation of Heteroarenes and Arenes

A trans-chelating chiral bisphosphine, PhTRAP, allows the ruthenium-catalyzed hydrogenation of various azoles to proceed with high enantioselectivity. The PhTRAP-ruthenium catalyst transformed indoles, pyrroles, imidazoles, and oxazoles into the correspon

Enzyme-catalyzed enantiomeric resolution of N-Boc-proline as the key-step in an expeditious route towards RAMP

For the preparation of both enantiomers of N-carbamoyl-2-methoxymethylpyrrolidine, the precursors of Enders' chiral auxiliaries, SAMP and RAMP, enzyme-catalyzed kinetic resolution of racemic N-carbamoyl, N-Boc, N-Cbz proline esters and prolinols were examined. B. licheniformis protease (subtilisin) preferentially hydrolyzed the (R)-carbamoylproline ester with an enantiomeric ratio (E) of 10. To a hydrophobic N-Cbz proline ester, subtilisin showed lower selectivity (E=2.8), and in contrast, a purified protease (isozyme A) from the earthworm showed the preference of (S)-enantiomer (E=13.6). In a practical sense, C. antarctica lipase B (Chirazyme L-2) was effective for the hydrolysis of both N-Boc and N-Cbz derivatives with E >100. The e.e. of (R)-N-carbamoyl-2-methoxymethylpyrrolidine was raised to be >99.9% by recrystallization at the N-Boc-prolinol stage, which was derived from the (R)-N-Boc-proline methyl ester (98.7% e.e.) through a preparative-scale enzyme-catalyzed resolution (49% yield) of the racemic substrate.