114676-93-6

Basic information

• Product Name: (2R,4R)-N-Boc-4-hydroxy-2-methylpyrrolidine
• Synonyms: (2r,4r)-n-boc-4-hydroxy-2-methylpyrrolidine;(2R,4R)-1-(tert-Butoxycarbonyl)-4-hydroxy-2-methylpyrrolidine;(2R,4R)-4-Hydroxy-2-methyl-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester;(2R,4R)-tert-Butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate;(2R, 4R)-4-Hydroxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester;tert-butyl (2R,4R)-4-hydroxy-2-methylpyrrolidine-1-carboxylate
• CAS NO: 114676-93-6
• Molecular Formula: C₁₀H₁₉NO₃
• Molecular Weight: 201.26
• Mol File: 114676-93-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 282 °C
• Flash Point: 125 °C
• Appearance: /
• Density: 1.094
• Refractive Index: 1.489
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (2R,4R)-N-Boc-4-hydroxy-2-methylpyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R)-N-Boc-4-hydroxy-2-methylpyrrolidine(114676-93-6)
• EPA Substance Registry System: (2R,4R)-N-Boc-4-hydroxy-2-methylpyrrolidine(114676-93-6)

Safety Data

• Hazardous Substances Data: 114676-93-6(Hazardous Substances Data)

Usage

General Description

(2R,4R)-N-Boc-4-hydroxy-2-methylpyrrolidine is a chemical compound with the molecular formula C10H19NO3. It is a derivative of pyrrolidine, a heterocyclic organic compound containing a five-membered ring with four carbon atoms and one nitrogen atom. (2R,4R)-N-Boc-4-hydroxy-2-methylpyrrolidine is specifically a Boc-protected hydroxyethylamine, which is commonly used in organic synthesis and medicinal chemistry. The Boc (tert-butyloxycarbonyl) group is a protecting group that can be removed under mild acidic conditions. This chemical has potential applications in the pharmaceutical industry, particularly in the synthesis of drug molecules where the Boc-protected hydroxyethylamine functionality is required.

InChI:InChI=1/C10H19NO3/c1-7-5-8(12)6-11(7)9(13)14-10(2,3)4/h7-8,12H,5-6H2,1-4H3/t7-,8-/m1/s1

Upstream product

• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 114676-67-4 (2S,4R)-1-Boc-4-[(t-butyldimethylsilyl)oxy]-2-(hydroxymethyl)pyrrolidine 
• 109431-87-0 (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate 
• 77-78-1 dimethyl sulfate 
• 114676-92-5 (2S,4R)-1-(tert-butoxycarbonyl)-4-<(tert-butyldimethylsilyl)oxy>-2-<<(methylsulfonyl)oxy>methyl>pyrrolidine 
• 114676-91-4 1-tert-butyl 2-methyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 132945-96-1 tert-butyl (2R,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-methylpyrrolidine-1-carboxylate 

Downstream Products

• 1027775-28-5 tert-butyl (2R)-2-methyl-4-oxopyrrolidine-1-carboxylate 
• 348165-61-7 C₁₇H₂₂N₂O₆ 
• 688810-07-3 (3R,5R)-5-methylpyrrolidin-3-ol 
• 114676-85-6 (2'R,4'S)-7-(4'-amino-2'-methylpyrrolidinyl)-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride 
• 114676-83-4 (2'R,4'S)-7-(4'-amino-2'-methylpyrrolidinyl)-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxoquinoline-3-carboxylic acid 
• 348165-62-8 (2R,4S)-tert-butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate 
• 859213-36-8 (2R,4R)-tert-butyl 2-methyl-4-(tosyloxy)pyrrolidine-1-carboxylate 

Relevant articles and documents

Design, synthesis and evaluation of novel 7H-pyrrolo[2,3-d]pyrimidin-4-amine derivatives as potent, selective and reversible Bruton's tyrosine kinase (BTK) inhibitors for the treatment of rheumatoid arthritis

A series of 7H-pyrrolo[2,3-d]pyrimidine derivatives were designed and synthesized as reversible BTK inhibitors, and evaluated their kinase selectivity, anti-proliferation against the B-cell lymphoma cell lines (Ramos, Jeko-1) and cell line BTK enhanced (Daudi) in vitro. Among them, compound 28a exhibited the most excellent potency (IC50 = 3.0 nM against BTK enzyme, 8.52 μM, 11.10 μM and 7.04 μM against Ramos, Jeko-1, Daudi cells, respectively), good kinase selectivity and inhibited BTK Y223 auto-phosphorylation and PLCγ2 Tyr1217 phosphorylation. Importantly, 28a showed efficacy anti-arthritic effect on collagen-induced arthritis (CIA) model in vivo. 28a 60 mg/kg dose level once a day group displayed markedly reduced joint damage and cellular infiltration without any bone and cartilage morphology change.

TRANS-3,5-DISUBSTITUTEDPYRROLIDINE: ORGANOCATALYST FOR anti-MANNICH REACTIONS

A compound of Formula I is disclosed, in which R is a substituent containing a hydrogen bond-forming atom within three atoms from the ring carbon to which the substituent is bonded; X is CH2, O, S or NR1, wherein R1 is a hydrocarbyl group or an amino-protecting group having one to about 18 carbon atoms; R2 is hydrido or a hydrocarbyl group containing one to about twelve carbon atoms; and R3 is hydrido or methyl, but both R2 and R3 are not hydrido when X is CH2 A molecule of Formula I and those in which R2 and R3 can both be hydrido (Formula X) functions as a catalyst in a Mannich reaction to asymmetrically form β-aminoaldehyde or β-aminoketone diastereomeric products having two chiral centers on adjacent carbon atoms and in which the anti-diastereomers are in excess over the syn-diastereomers. Methods for carrying out those syntheses are also disclosed.

Regioselective directed lithiation of N-Boc 3-hydroxypyrrolidine. Synthesis of 2-substituted 4-hydroxypyrrolidines

N-Boc 3-hydroxypyrrolidine 1 undergoes directed C-lithiation at C5 and not, as previously reported, at C2; the resulting dilithiated intermediate 6 has been trapped by a range of electrophiles to give 2-substituted 4-hydroxypyrrolidines 7.