59378-81-3

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 2-(hydroxymethyl)-, 1,1-dimethylethyl ester, (±)-
• CAS NO: 59378-81-3
• Molecular Formula: C10H19NO3
• Molecular Weight: 201.266
• Mol File: 59378-81-3.mol
• Article Data: 51

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 2-(hydroxymethyl)-, 1,1-dimethylethyl ester, (±)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 2-(hydroxymethyl)-, 1,1-dimethylethyl ester, (±)-(59378-81-3)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 2-(hydroxymethyl)-, 1,1-dimethylethyl ester, (±)-(59378-81-3)

Safety Data

• Hazardous Substances Data: 59378-81-3(Hazardous Substances Data)

Usage

Chemical structure

1-Pyrrolidinecarboxylic acid, 2-(hydroxymethyl)-, 1,1-dimethylethyl ester

Type of compound

Tert-butoxycarbonyl (Boc) protected form of the amino acid proline

Use in organic synthesis

As a protecting group for the amino group of proline, allowing for selective manipulation of other functional groups without affecting the proline residue

Use in industry

Production of pharmaceuticals and fine chemicals, as well as in the field of peptide synthesis

Physical properties

Colorless to slightly yellow solid, soluble in organic solvents such as methanol and dichloromethane.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1315053-73-6 C₅H₁₁NO 
• 43041-12-9 methyl (2R)-pyrrolidine-2-carboxylate 
• 147-85-3 L-proline 
• 344-25-2 D-Prolin 
• 1301760-11-1 C₁₅H₂₅NO₅ 
• 101555-60-6 2-(R)-carboxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 15761-39-4 N-tert-butoxycarbonyl-proline 
• 145681-01-2 (+/-)-N-tert-butoxycarbonylproline methyl ester 
• 73323-65-6 1-(tert-butyl) 2-methyl (R)-pyrrolidine-1,2-dicarboxylate 
• 68832-13-3 D-prolinol 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 

Downstream Products

• 769961-18-4 (R)-2-(5-nitro-2-trifluoromethyl-phenoxymethyl)-1-(tert-butylcarbonyl)pyrrolidine 
• 952490-83-4 (R)-2-(5-nitro-2-pentafluoroethyl-phenoxymethyl)-1-(tert-butylcarbonyl)pyrrolidine 
• 59378-82-4 N-(tert-butoxycarbonyl)pyrrolidine-2-carboxaldehyde 
• 73365-02-3 tert-butoxycarbonyl-D-prolinal 
• 916483-47-1 tert-butyl (2R)-2-[({4-[(1-{2-[(2,3-difluorophenyl)amino]-2-oxoethyl}-1H-pyrazol-4-yl)amino]-7-ethoxyquinazolin-5-yl}oxy)methyl]pyrrolidine-1-carboxylate 
• 955359-80-5 1,1-dimethylethyl (2S)-2-{[4-[(4-chlorophenyl)methyl]-1-oxo-2(1H)-phthalazinyl]methyl}-1-pyrrolidinecarboxylate 
• 60419-23-0 (R)-(-)-1-(2-pyrrolidinylmethyl)pyrrolidine 
• 955360-43-7 4-[(4-chlorophenyl)methyl]-2-{[(2R)-2-pyrrolidinyl]methyl}-1(2H)-phthalazinone hydrochloride salt 
• 1228017-64-8 C₁₆H₂₁Cl₂NO₃ 
• 924906-93-4 (R)-2-(5-fluoro-2-methoxyphenoxymethyl)-N-BOC-pyrrolidine 
• 1039826-29-3 (R)-tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate 
• 259538-74-4 tert-Butyl (2 R)-2-{[3-(cyanomethyl)phenoxy]methyl}-1-pyrrolidinecarboxylate 
• 575467-47-9 (E)-1-((S)-2-((Pyrrolidin-1-yl)methyl)pyrrolidin-1-yl)-3-(4-(trifluoromethyl)phenyl)propenone 
• 786684-90-0 tert-butyl (2R)-2-{[(7-(benzyloxy)-3-{[(2,2-dimethylpropanoyl)oxy]methyl}-4-oxo-3,4-dihydroquinazolin-5-yl)oxy]methyl}pyrrolidine-1-carboxylate 

Relevant articles and documents

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.

Pyrrolidine-Oxadiazolone Conjugates as Organocatalysts in Asymmetric Michael Reaction

Pyrrolidine-oxadiazolone based organocatalysts are envisaged, synthesized, and utilized for asymmetric Michael reactions. Results of the investigations suggest that some of the catalysts are indeed efficient for stereoselective 1,4-conjugated Michael additions (dr: >97:3, ee up to 99%) in high chemical yields (up to 97%) often in short reaction time. As an extension, one enantiopure Michael adduct has been utilized to synthesize optically active octahydroindole.

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