92645-06-2

Basic information

• Product Name: 2-N-CBZ-AMINO-CYCLOHEXANOL
• Synonyms: 2-N-CBZ-AMINO-CYCLOHEXANOL;benzyl 2-hydroxycyclohexylcarbamate
• CAS NO: 92645-06-2
• Molecular Formula: C₁₄H₁₉NO₃
• Molecular Weight: 249.30556
• Mol File: 92645-06-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-N-CBZ-AMINO-CYCLOHEXANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-N-CBZ-AMINO-CYCLOHEXANOL(92645-06-2)
• EPA Substance Registry System: 2-N-CBZ-AMINO-CYCLOHEXANOL(92645-06-2)

Safety Data

• Hazardous Substances Data: 92645-06-2(Hazardous Substances Data)

Upstream product

• 38898-70-3 cis-2-amino-cyclohexanol-⁽¹⁾ 
• 501-53-1 benzyl chloroformate 
• 1262306-22-8 benzyloxycarbonylamino-4-chlorobenzoate 
• 110-83-8 cyclohexene 
• 931-16-8 (+/-)-trans-2-aminocyclohexanol 
• 286-20-4 cyclohexane-1,2-epoxide 
• 6850-38-0 2-aminocyclohexanol 
• 2425-33-4 2-bromocyclocyclohexanol 
• 286-20-4 cyclohexene oxide 

Downstream Products

• 100956-49-8 (+/-)-3-oxo-(3ar,7ac)-hexahydro-benzoxazole-3-carboxylic acid benzyl ester 
• 101105-37-7 hexahydro-benzooxazole-3-carboxylic acid benzyl ester 
• 112689-63-1 hexahydro-spiro[benzooxazole-2,1'-cyclohexane]-3-carboxylic acid benzyl ester 
• 102449-47-8 2-phenyl-(3ar,7ac)-hexahydro-benzooxazole-3-carboxylic acid benzyl ester 
• 102076-03-9 2-methyl-hexahydro-benzooxazole-3-carboxylic acid benzyl ester 
• 113186-20-2 hexahydro-spiro[benzooxazole-2,1'-cyclopentane]-3-carboxylic acid benzyl ester 
• 101599-08-0 2,2-dimethyl-hexahydro-benzooxazole-3-carboxylic acid benzyl ester 
• 187333-96-6 (1S,2R)-2-(benzyloxycarbonylamino)cyclohexan-1-ol 
• 187334-05-0 (1S,2R-2-hydroxy-cyclohexyl)-carbamic acid benzyl ester 
• 100956-93-2 (+/-)-(trans-2-chlorocarbonyloxy-cyclohexyl)-carbamic acid benzyl ester 
• 134071-00-4 Butyric acid (1S,2S)-2-benzyloxycarbonylamino-cyclohexyl ester 
• 1448438-56-9 (1S,2S)-2-(benzyloxycarbonylamino)cyclohexyl 3-phenylpropanoate 
• 134108-76-2 (1R,2R)-2-hydroxycyclohexylcarbamic acid benzyl ester 
• 31236-61-0 (+/-)-2-cyclohexanone 

Relevant articles and documents

New procedure for the preparation of (1 R,2 R)-2-[(R)-3-(benzyloxy)pyr- rolidin-1-yl]cyclohexanol

A novel route to an intermediate of vernakalant, (1R,2R)-2-[(R)-3- (benzyloxy)pyrrolidin-1-yl]cyclohexanol from ethyl (R)-4-chloro-3- hydroxybutanoate is described. It was found that the key intermediate (R)-4-(benzyloxy)-1-[(1R,2R)-2-(tert-butyldimethylsiloxy)cyclohexyl] pyrrolidin-2-one could be isolated with high dia-stereomeric excess (up to 99% de) from its isomer by column chromatography alone, without further chemical resolution. Georg Thieme Verlag Stuttgart. New York.

IMPROVED AMINOHYDROXYLATION OF ALKENES

The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.

Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction

Ethyl-(7), benzyl-(8), tert-butyl-(9), and fluorenylmethyl-4- chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.

A General Route to the Synthesis of N-Protected 1-Substituted and 1,2-Disubstituted Taurines

N-Benzyloxycarbonyl protected α-substituted and αβ- disubstituted taurines were synthesized from olefins and epoxides via N-benzyloxycarbonylamino alcohol thioacetates as key intermediates. They are important sulfur analogues of naturally occurring amino acids and building blocks for the synthesis of α-substituted and α,β- disubstituted β-sulfonopeptides.

Enzymatic resolution of (±)-cis-2-aminocyclopentanol and (±)-cis-2- aminocyclohexanol

(±)-cis-N-Benzyloxycarbonyl-2-aminocyclopentanol was efficiently resolved by O-acylation with Pseudomonas cepacia lipase, as was (±)-cis-N- benzyloxycarbonyl-2-aminocyclohexanol when Candida antarctica lipase was used.

Preparation of 2-oxazolidinones by intramolecular nucleophilic substitution

Treatment of N-alkoxycarbonyl, N-benzyl protected β-amino alcohols with triphenylphosphine and hexachloroethane in 1,2-dichloroethane induces cyclization to 2-oxazolidinones, which are formed by intramolecular attack with inversion of configuration at the secondary alcohol. In contrast, mono N-substituted alkyl carbamates undergo chlorination under the same conditions.

Enzymatic resolution of (±)-trans-2-aminocyclohexanol and (±) trans-2-aminocyclopentanol

Candida antarctica lipase (CAL) catalyzes the resolution of (±)-trans-2-aminocyclohexanol by alkoxycarbonylation or acylation reactions. Besides, N-benzyloxycarbonyl derivatives of (±)-trans-2-aminocyclohexanol and (±)-trans-2-aminocyclopentanol are efficiently resolved through O-acylation by Pseudomonas cepacia lipase (PSL).

STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED PIPECOLIC ACIDS

The stereoselective synthesis of Δ4,5-pipecolic acid derivatives is described.The key step in the sequence is a sigmatropic rearrangement.