1476776-55-2

Basic information

• Product Name: tert-butyl (S)-3-(4-bromophenyl)piperidine-1-carboxylate
• Synonyms: tert-butyl (S)-3-(4-bromophenyl)piperidine-1-carboxylate;(S)-tert-butyl3-(4-bromophenyl)piperidine-1-carboxylate;tert-Butyl (3s)-3-(4-bromophenyl)-piperidine-1-carboxylate;(3S)-3-(4-Bromophenyl)-1-piperidinecarboxylic acid 1,1-dimethylethylester
• CAS NO: 1476776-55-2
• Molecular Formula: C₁₆H₂₂BrNO₂
• Molecular Weight: 340.27
• EINECS: 1533716-785-6
• Product Categories: API
• Mol File: 1476776-55-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 398.5±42.0 °C(Predicted)
• Appearance: /
• Density: 1.283±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -1.84±0.40(Predicted)
• CAS DataBase Reference: tert-butyl (S)-3-(4-bromophenyl)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (S)-3-(4-bromophenyl)piperidine-1-carboxylate(1476776-55-2)
• EPA Substance Registry System: tert-butyl (S)-3-(4-bromophenyl)piperidine-1-carboxylate(1476776-55-2)

Safety Data

• Hazardous Substances Data: 1476776-55-2(Hazardous Substances Data)

Usage

Description

tert-butyl (S)-3-(4-bromophenyl)piperidine-1-carboxylate is an organic compound that serves as a crucial intermediate in the synthesis of Niraparib, a novel oral poly(ADP-ribose)polymerase (PARP) inhibitor. tert-butyl (S)-3-(4-bromophenyl)piperidine-1-carboxylate plays a significant role in the development of pharmaceuticals targeting BRCA-1 and -2 mutant tumors.

Uses

Used in Pharmaceutical Industry:
tert-butyl (S)-3-(4-bromophenyl)piperidine-1-carboxylate is used as an intermediate for the synthesis of Niraparib, a novel oral PARP inhibitor for the treatment of BRCA-1 and -2 mutant tumors. Its role in the development of this therapeutic agent is essential, as it contributes to the efficacy of Niraparib in targeting and treating these specific types of cancer.

Upstream product

• 6340-79-0 4-oxo-4-(4-bromophenyl)butanoic acid 
• 1284448-67-4 isopropyl 4-(4-bromophenyl)-4-oxobutanoate 
• 1476776-39-2 isopropyl 3-(2-(4-bromophenyl)oxiran-2-yl)-propanoate 
• 1476776-40-5 isopropyl 4-(4-bromophenyl)-5-oxopentanoate 
• 1476776-44-9 (S)-5-(4-bromophenyl)piperidin-2-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1476776-53-0 (S)-3-(4-bromophenyl)piperidin-1-ium 4-methylbenzenesulfonate 
• 1335523-82-4 4-(3S-piperidine-3-yl)bromobenzene 
• 1476776-62-1 C₁₁H₁₆BrNO 
• 1476776-64-3 (S)-tert-butyl (2-(4-bromophenyl)-5-hydroxypentyl)carbamate 
• 1476776-66-5 (S)-4-(4-bromophenyl)-5-((tert-butoxycarbonyl)amino)pentyl methanesulfonate 
• 108-86-1 bromobenzene 
• 1476776-61-0 C₁₁H₁₃BrO₂ 
• 1008-88-4 3-phenylpyridine 

Downstream Products

• 1038915-73-9 2-[4-((3S)-3-piperidinyl)phenyl]-2H-indazole-7-carboxamide p-toluenesulfonic acid salt 
• 1196713-67-3 2-[4-((3S)-(tertbutoxycarbonyl)piperidin-3-yl)phenyl]-2H-indazole-7-carboxylic acid methyl ester 
• 1038915-60-4 (3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine 

Relevant articles and documents

DEUTERATED (S)-2-(4-(PIPERIDIN-3-YL)PHENYL)-2H-INDAZOLE-7-CARBOXAMIDE

A deuterated compound having the structure of Formula I: or a pharmaceutically acceptable salt, solvate, or prodrug thereof; or a salt of a prodrug thereof; or a hydrate or polymorph thereof; whereinY1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, Y9, Y9', Y10, Y10', Y11,

Preparation method of chiral intermediate of niraparib

The invention discloses a novel synthetic method for preparing a chiral intermediate of niraparib. The method comprises the following steps: taking 4-bromophenylacetic acid and chiral substituted oxazolone as starting materials; and carrying out amide condensation, Michael addition, hydrolysis, reduction and intramolecular cyclization to obtain the intermediate (VII). The preparation method is low in cost, raw materials are easily obtained, the yield is high, and the synthetic method is suitable for industrialized production.

Process development of C-N cross-coupling and enantioselective biocatalytic reactions for the asymmetric synthesis of niraparib

Process development of the synthesis of the orally active poly(ADP-ribose)polymerase inhibitor niraparib is described. Two new asymmetric routes are reported, which converge on a high-yielding, regioselective, copper-catalyzed Narylation of an indazole derivative as the late-stage fragment coupling step. Novel transaminase-mediated dynamic kinetic resolutions of racemic aldehyde surrogates provided enantioselective syntheses of the 3-aryl-piperidine coupling partner. Conversion of the C-N cross-coupling product to the final API was achieved by deprotection and salt metathesis to isolate the desired crystalline salt form.