329910-39-6

Basic information

• Product Name: (1S,3S)-N-BOC-1-AMINOCYCLOPENTANE-3-CARBOXYLIC ACID METHYL ESTER
• Synonyms: (1S,3S)-N-BOC-1-AMINOCYCLOPENTANE-3-CARBOXYLIC ACID METHYL ESTER;(1S,3S)-N-TERT-BUTOXYCARBONYL-1-AMINOCYCLOPENTANE-3-CARBOXYLIC ACID METHYL ESTER;Cyclopentanecarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester, (1S,3S)- (9CI);(1S,3S)-N-boc-1-Aminocyclopentane-3-carboxylicacidmethylester(e.e.);(1S,3S)-N-BOC-1-AMINOCYCLOPENTANE-3-CARBO-XYLIC ACID METHYL ESTER 95% (98% E.E.);(1S,3S)-N-BOC-1-Aminocyclopentane-3-carboxylic acid methyl ester, 98% ee, 95%;methyl (1S,3S)-3-{[(tert-butoxy)carbonyl]amino}cyclopentane-1-carboxylate;(1S,3S)-1-(Boc-amino)cyclopentane-3-carboxylic acid methyl ester
• CAS NO: 329910-39-6
• Molecular Formula: C12H21NO4
• Molecular Weight: 243.3
• Product Categories: N-BOC
• Mol File: 329910-39-6.mol

Chemical Properties

• Boiling Point: 386.17°C (rough estimate)
• Flash Point: 154.5°C
• Appearance: /
• Density: 1.1177 (rough estimate)
• Vapor Pressure: 0.000152mmHg at 25°C
• Refractive Index: 1.4596 (estimate)
• CAS DataBase Reference: (1S,3S)-N-BOC-1-AMINOCYCLOPENTANE-3-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3S)-N-BOC-1-AMINOCYCLOPENTANE-3-CARBOXYLIC ACID METHYL ESTER(329910-39-6)
• EPA Substance Registry System: (1S,3S)-N-BOC-1-AMINOCYCLOPENTANE-3-CARBOXYLIC ACID METHYL ESTER(329910-39-6)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 329910-39-6(Hazardous Substances Data)

Usage

Chemical Properties

white needle-like crystals

InChI:InChI=1/C12H21NO4/c1-12(2,3)17-11(15)13-9-6-5-8(7-9)10(14)16-4/h8-9H,5-7H2,1-4H3,(H,13,15)/t8-,9-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 147698-10-0 (S)-3--(methoxycarbonyl)cyclopentene 
• 1085842-51-8 methyl (1S,3S)-3-aminocyclopentane-1-carboxylate hydrochloride 
• 147698-08-6 (S)-6-Imidazol-1-yl-6-oxo-5-(9-phenyl-9H-fluoren-9-ylamino)-hexanoic acid methyl ester 
• 147698-06-4 1-tert-Butyl 6-methyl (S)-2-[N-(9-phenylfluoren-9-yl)amino]hexandioate 
• 215182-84-6 (1S,3R/S)-1-[N-(9-Phenylfluoren-9-yl)amino]-2-oxo-3-(methoxycarbonyl)cyclopentane 
• 147698-07-5 (S)-2-hexanedioic acid γ-methyl ester 
• 168683-02-1 (1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate 
• 229613-83-6 (–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride 
• 251327-00-1 methyl (4S)-4-[(tert-butyloxycarbonyl)amino]cyclopent-1-ene-1-carboxylate 

Downstream Products

• 71376-02-8 (+)-trans-(1S,3S)-3-aminocyclopentane-1-carboxylic acid 
• 1085842-51-8 methyl (1S,3S)-3-aminocyclopentane-1-carboxylate hydrochloride 
• 167081-31-4 ((1S,3S)-3-hydroxymethylcyclopentyl)carbamic acid tert-butyl ester 
• 220497-66-5 (1S,3S)-3-(9-fluorenylmethoxycarbonylamino)cyclopentanecarboxylic acid 

Relevant articles and documents

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Highly selective directed hydrogenation of enantiopure 4-(tert-butoxycarbonylamino)cyclopent-1-enecarboxylic acid methyl esters

The use of both N-tert-butoxycarbonylamino- and hydroxyl-directed hydrogenation methodology to yield essentially single diastereomers of 3-(tert-butoxycarbonylamino)-4-hydroxycyclopentanecarboxylic acid methyl esters and 3-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid methyl esters is described. These results incorporate the first reported carbamate-directed hydrogenations of functionalised cyclopentenes.

Chirospecific Synthesis of (1S,3R)-1-Amino-3-(hydroxymethyl)cyclopentane, Precursor for Carbocyclic Nucleoside Synthesis. Dieckmann Cyclization with an α-Amino Acid

Carbocyclic nucleosides are important isosters of nucleosides possessing a variety of antiviral and antineoplastic activities.We report here a new method for the chirospecific synthesis of (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane.This compound is a key precursor for the synthesis of some carbocyclic nucleosides.The method involves (1) an improved synthesis of (S)-2-aminoadipic acid; (2) Dieckmann cyclization of this α-amino acid to an aminocyclopentanone; and (3) elaboration of the latter to the target (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane.The starting (S)-2-aminoadipic acid δ-methyl ester was prepared enantiomerically pure from (S)-aspartic acid in 51percent overall yield.Dieckmann condensation converted this amino acid to a (methoxycarbonyl)-cyclopentanone, and reduction of the ketone followed by elimination yielded (S)-3--1-(methoxycarbonyl)cyclopentene.Reduction of the double bond gave a mixture of the cis and trans diastereomers.This mixture was converted to a single diastereomer by epimerization and trapping of the cis isomer as (1S,4R)-2-(9-phenylfluoren-9-yl)-2-azabicycloheptan-3-one.Hydrolytic cleavage of the lactam followed by reduction gave (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane.