207729-04-2

Basic information

• Product Name: Carbamic acid, [(1R,3R)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester, rel-
• Synonyms: Carbamic acid, [(1R,3R)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester, rel-;rel-N-[(1R,3R)-3-Hydroxycyclopentyl]carbamic acid tert-butyl ester;trans-3-N-Boc-aMinocyclopentanol;(1R,3S)-tert-butyl(3-hydroxycyclopentyl)catbaMte;CarbaMic acid,N-[(1R,3R)-3-hydroxycyclopentyl]-, 1,1-diMethylethyl ester, rel-;tert-Butyl ((1R,3R)-3-hydroxycyclopentyl)carbaMate;trans-tert-butyl 3-hydroxycyclopentylcarbamate;tert-butyl N-[trans-3-hydroxycyclopentyl]carbamate
• CAS NO: 207729-04-2
• Molecular Formula: C10H19NO3
• Molecular Weight: 201.27
• Product Categories: N-BOC
• Mol File: 207729-04-2.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 321℃
• Flash Point: 148℃
• Appearance: /
• Density: 1.08
• CAS DataBase Reference: Carbamic acid, [(1R,3R)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester, rel-(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1R,3R)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester, rel-(207729-04-2)
• EPA Substance Registry System: Carbamic acid, [(1R,3R)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester, rel-(207729-04-2)

Safety Data

• Hazardous Substances Data: 207729-04-2(Hazardous Substances Data)

Usage

General Description

Carbamic acid, [(1R,3R)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester, rel- is a chemical compound used in the pharmaceutical industry. It is commonly known for its use as a pharmaceutical intermediate and a molecular building block. Carbamic acid, [(1R,3R)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester, rel- is derived from carbamic acid and features a hydroxycyclopentyl group bonded to a 1,1-dimethylethyl ester functional group. Its stereochemistry is designated as (1R,3R) and it is primarily used in the synthesis of various pharmaceutical compounds.

Upstream product

• 930-30-3 cyclopent-2-enone 
• 847416-99-3 tert-butyl N-(3-oxocyclopentyl)carbamate 
• 189625-14-7 (2S,4R)-acetic acid 4-tert-butoxycarbonylaminocyclopent-2-enyl ester 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 154802-92-3 tert-butyl [(1S,4S)-4-hydroxycyclopent-2-en-1-yl]carbamate 
• 60176-77-4 (1S,4R)-4-hydroxy-2-cyclopentenyl acetate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 16326-97-9 1,3-dihydroxycyclopentane 
• 167465-99-8 (1S,3R)-3-hydroxycyclopentyl-1-carbamic acid tert-butyl ester 

Downstream Products

• 946593-67-5 (1S,3S)-3-aminocyclopentan-1-ol 
• 1197398-99-4 tert-butyl N-[trans-3-aminocyclopentyl]carbamate 
• 1197398-99-4 C₁₀H₂₀N₂O₂ 
• 847416-99-3 tert-butyl N-(3-oxocyclopentyl)carbamate 
• 13725-38-7 3-aminocyclopentan-1-ol 
• 124555-33-5 cis-3-aminocyclopentan-1-ol hydrochloride 

Relevant articles and documents

Asymmetric Phase-Transfer Catalytic aza-Michael Addition to Cyclic Enone: Highly Enantioselective and Diastereoselective Synthesis of Cyclic 1,3-Aminoalcohols

The highly enantioselective aza-Michael reaction of tert-butyl β-naphthylmethoxycarbamate to cyclic enones has been accomplished by using a new cinchona alkaloid derived C(9)-urea ammonium catalyst under phase-transfer catalysis conditions with up to 98% ee at 0 °C. The resulting aza-Michael adducts can be converted to versatile intermediates by selective deprotection and the cyclic 1,3-aminoalcohols by diastereoselective reduction with up to 32:1, which have been widely used as important pharmacophores in pharmaceutical development.

Method for preparing (1R, 3S)-3-aminocyclopentanol hydrochloride

The invention discloses a method for preparing (1R, 3S) 3-aminocyclopentanol hydrochloride, belongs to the field of organic chemical synthesis, and provides a process route to overcome the defects ofhigh price, difficulty in chiral control and the like in the prior art. The process route comprises the following steps: 1) oxidizing tert-butyl carbonate hydroxylamine into tert-butyl carbonate nitrosyl under the catalysis of copper chloride and 2-ethyl-2-oxazoline, then carrying out a hetero Diels-Alder reaction with cyclopentadiene in situ; 2) selectively reducing nitrogen-oxygen bonds in a zinc powder-acetic acid reaction system; 3) under the catalysis of lipase, reacting with vinyl acetate to optically and selectively realize chiral resolution; 4) reducing double bonds through palladium carbon hydrogenation; 5) under the alkaline condition of lithium hydroxide-methanol, performing deacetylation protection; and 6) removing tert-butyl carbonate protection in a hydrogen chloride isopropanol acid solution prepared from acetyl chloride and isopropanol in situ, and forming hydrochloride in situ to obtain a target product. The synthetic method has the beneficial effects that the synthetic method has the characteristics of novel and short route, high optical purity, low cost and the like.

Preparation method of (1R,3S)-3-amino cyclopentanol hydrochloride

The invention provides a preparation method of (1R,3S)-3-amino cyclopentanol hydrochloride. A urea peroxide-trifluoroacetic anhydride system is adopted as an oxidizing agent, and a compound I is subjected to oxidation reaction so as to generate a compound II and a compound II', so that the use of an oxidizing agent with high price and big risk is avoided. Hydrogen chloride obtained through esterification reaction of isopropanol and an acyl chloride compound is subjected to de-protection reaction with a compound III, so that the process stability is good compared with the way of directly feeding hydrogen chloride and carrying out de-protection reaction on the hydrogen chloride and the compound III, the condition that the (1R,3S)-3-amino cyclopentanol hydrochloride can be smoothly separatedout from a reaction solution is ensured, and the method is convenient to operate and friendly to the work environment. In addition, the preparation method provided by the invention is high in productyield and purity, low in production cost, high in safety, simple to operate, and suitable for large-scale production.