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
• Article Data: 8

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 
• 931-16-8 (+/-)-trans-2-aminocyclohexanol 
• 286-20-4 cyclohexane-1,2-epoxide 
• 6850-38-0 2-aminocyclohexanol 
• 110-83-8 cyclohexene 
• 2425-33-4 2-bromocyclocyclohexanol 
• 286-20-4 cyclohexene oxide 
• 1262306-22-8 benzyloxycarbonylamino-4-chlorobenzoate 

Downstream Products

• 100956-49-8 (+/-)-3-oxo-(3ar,7ac)-hexahydro-benzoxazole-3-carboxylic acid benzyl ester 
• 100956-93-2 (+/-)-(trans-2-chlorocarbonyloxy-cyclohexyl)-carbamic 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 
• 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 
• 900513-88-4 (1R,2R)-2-[(R)-3-(benzyloxy)pyrrolidin-1-yl]cyclohexanol 
• 1360871-01-7 (R)-4-(benzyloxy)-1-[(1R,2R)-2-(tert-butyldiphenylsiloxy)cyclohexyl]pyrrolidin-2-one 

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.

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.