163765-44-4

Basic information

• Product Name: (R)-4-Boc-2-methylpiperazine
• Synonyms: (R)-METHYL-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;(R)-N-BOC-2-METHYLPIPERAZINE;(R)-N4-BOC-2-METHYLPIPERAZINE;TERT-BUTYL (R)-3-METHYL-1-PIPERAZINECARBOXYLATE;(R)-4-N-BOC-2-METHYLPIPERAZINE;(R)-4-BOC-2-METHYLPIPERAZINE;(R)-3-METHYL-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;(R)-1-BOC-3-METHYLPIPERAZINE
• CAS NO: 163765-44-4
• Molecular Formula: C₁₀H₂₀N₂O₂
• Molecular Weight: 200.28
• Product Categories: Piperazine series;pharmacetical;Piperaizine;Piperazines
• Mol File: 163765-44-4.mol
• Article Data: 17

Chemical Properties

• Melting Point: 40-45 °C
• Boiling Point: 268.7 °C at 760 mmHg
• Flash Point: 223 °F
• Appearance: White/Crystalline Powder
• Density: 0.997 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 8.52±0.40(Predicted)
• CAS DataBase Reference: (R)-4-Boc-2-methylpiperazine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-Boc-2-methylpiperazine(163765-44-4)
• EPA Substance Registry System: (R)-4-Boc-2-methylpiperazine(163765-44-4)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41-36/37/38
• Safety Statements: 26-39-37/39
• WGK Germany: 3
• F: 10-34
• Hazardous Substances Data: 163765-44-4(Hazardous Substances Data)

Usage

Description

(R)-4-Boc-2-methylpiperazine, also known as (R)-1-(tert-butoxycarbonyl)-2-methylpiperazine, is a chiral reagent derived from piperazine, a heterocyclic amine. It is characterized by its white solid appearance and is a crucial intermediate in the synthesis of various pharmaceutical compounds. The presence of the Boc protecting group and the methyl substituent at the 2-position imparts unique chemical properties and reactivity to this compound, making it a valuable building block in organic synthesis.

Uses

Used in Pharmaceutical Industry:
(R)-4-Boc-2-methylpiperazine is used as a key intermediate in the synthesis of pharmaceutical compounds for various therapeutic applications. Its unique structure allows for the development of new drugs with improved potency, selectivity, and pharmacokinetic properties.
Used in Organic Synthesis:
(R)-4-Boc-2-methylpiperazine is used as a reagent in organic synthesis for the preparation of a wide range of organic compounds. Its versatility as a building block enables the synthesis of complex molecules with diverse functional groups and structural features.
Used in the Synthesis of Inhibitors:
(R)-4-Boc-2-methylpiperazine is used as a precursor in the synthesis of orally bioavailable inhibitors of 11-β-hydroxysteroid dehydrogenase (11-β-HSD). These inhibitors have potential applications in the treatment of metabolic disorders, such as type 2 diabetes and obesity, by modulating the activity of 11-β-HSD enzymes.
Used in Drug Development:
(R)-4-Boc-2-methylpiperazine is used as a starting material in drug development for the discovery of novel therapeutic agents. Its unique chemical properties and reactivity make it an attractive candidate for the design and synthesis of new drugs with improved efficacy and safety profiles.

Upstream product

• 75336-86-6 (2R)-methylpiperazine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 120737-59-9 3-methyl-piperazine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 442868-88-4 (R)-4-{(S)-1-[4-(Benzo[1,3]dioxole-5-sulfonyl)-phenyl]-ethyl}-3-methyl-piperazine-1-carboxylic acid tert-butyl ester 
• 1242138-67-5 (R)-tert-butyl 4-(4-acetylphenylsulfonyl)-3-methylpiperazine-1-carboxylate 
• 203180-30-7 (R)-1-{(S)-1-[4-(Benzo[1,3]dioxole-5-sulfonyl)-phenyl]-ethyl}-2-methyl-4-piperidin-4-yl-piperazine 
• 203180-28-3 4-((R)-4-{(S)-1-[4-(Benzo[1,3]dioxole-5-sulfonyl)-phenyl]-ethyl}-3-methyl-piperazin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester 
• 203180-27-2 (R)-1-{(S)-1-[4-(Benzo[1,3]dioxole-5-sulfonyl)-phenyl]-ethyl}-2-methyl-piperazine 
• 849107-17-1 4-(4-chloro-phenyl)-3-(R)-methyl-piperazine-1-carboxylic acid tert-butyl ester 
• 871836-24-7 (3R)-4-[(2S)-2-(2-methoxy-4-methoxycarbonylphenoxy)propionyl]-3-methylpiperazine-1-carboxylic acid tert-butyl ester 
• 902766-06-7 tert-butyl (3R)-4-(1,1'-biphenyl-4-ylcarbonyl)-3-methylpiperazine-1-carboxylate 
• 878809-85-9 (3R)-4-[2-chloro-6-(4-fluoro-phenyl)-pyrimidin-4-yl]-3-methyl-piperazine-1-carboxylic acid tert-butyl ester 
• 911405-95-3 C₂₅H₃₂FN₃O₃ 
• 1163793-25-6 1-benzyl 4-(tert-butyl) (R)-2-methylpiperazine-1,4-dicarboxylate 
• 623586-02-7 (2R)-1,2-dimethylpiperazine 

Relevant articles and documents

Preparation method of tyrosine kinase inhibitor AZD3759

The invention provides a preparation method of a tyrosine kinase inhibitor AZD3759, and relates to the field of medicinal chemistry. The preparation method comprises the following steps: by taking 3,4-dihydro-7-methoxy-4-oxoquinazoline-6-alcohol acetate as a raw material, carrying out a chlorination reaction and a hydrolysis reaction to obtain 4-chloro-7-methoxyquinazoline-6-alcohol (a compound 3); taking (R)-(-)-2-methylpiperazine as a raw material, and obtaining (R)-4-chlorocarbonyl-3-tert-butyl formate (compound 6) through a nucleophilic addition-elimination reaction and a chloroformylation reaction; carrying out an esterification reaction on the compound 3 and the compound 6 to obtain a compound 7; carrying out a Boc removal reaction and a methylation reaction on the compound 7 to obtain a compound 9; and carrying out alkylation reaction on the compound 9 and 2-fluoro-3-chloroaniline to obtain AZD3759. The method has the advantages of cheap and accessible raw materials and lower cost; sodium cyanoborohydride is not used in the reaction process, so that the method is more environment-friendly and is beneficial to industrial large-scale production.

1,4-Palladium Shift/C(sp3)-H Activation Strategy for the Remote Construction of Five-Membered Rings

1,n-Metal shift is an elegant alternative approach enabling the functionalization of remote C-H bonds from simple precursors. In this work, we report a novel and simple Pd0-catalyzed domino reaction involving 1,4-palladium shift and C(sp3)-H activation and leading to (fused) five-membered rings. This method allowed access to a broad range of valuable arylidene γ-lactams and indanones and was applied to the formal synthesis of (-)-pyrrolam.

CHEMOKINE RECEPTOR ANTAGONISTS AND METHODS OF USE THEREOF

Disclosed are novel compounds and a method of treating a disease associated with aberrant leukocyte recruitment and/or activation. The method comprises administering to a subject in need an effective amount of a compound represented by: or physiologically acceptable salt thereof.