185426-13-5

Basic information

• Product Name: Carbamic acid, [(2R)-2-hydroxybutyl]-, 1,1-dimethylethyl ester (9CI)
• Synonyms: Carbamic acid, [(2R)-2-hydroxybutyl]-, 1,1-dimethylethyl ester (9CI)
• CAS NO: 185426-13-5
• Molecular Formula: C₉H₁₉NO₃
• Molecular Weight: 189.25206
• Product Categories: N-BOC
• Mol File: 185426-13-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, [(2R)-2-hydroxybutyl]-, 1,1-dimethylethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(2R)-2-hydroxybutyl]-, 1,1-dimethylethyl ester (9CI)(185426-13-5)
• EPA Substance Registry System: Carbamic acid, [(2R)-2-hydroxybutyl]-, 1,1-dimethylethyl ester (9CI)(185426-13-5)

Safety Data

• Hazardous Substances Data: 185426-13-5(Hazardous Substances Data)

Upstream product

• 185426-07-7 (1S,2R,1'R)-(-)-N-<2-(1'-tert-butoxycarbonylaminomethylpropoxy)-1-methyl-2-phenylethyl>formamide 
• 853737-95-8 N-2-nitrobenzenesulfonyl-((R)-2-hydroxybutyl)carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 

Relevant articles and documents

Direct catalytic synthesis of enantiopure 5-substituted oxazolidinones from racemic terminal epoxides

(Chemical Equation Presented) A venerable scaffold for asymmetric synthesis and drug development, chiral 5-substituted oxazolidinones are obtained in almost enantiomerically pure form (up to 99.9% ee) starting from racemic terminal epoxides. The salient features of this process include the very simple and convenient experimental protocol and the employment of a readily accessible catalyst and inexpensive, easily handled starting materials. An enantioconvergent approach for the total conversion of racemic epoxide into a single stereoisomeric oxazolidinone is also described.

Diastereo- and enantioselective synthesis of vicinal amino alcohols by oxa Michael addition of N-formylnorephedrine to nitro alkenes

The first intermolecular asymmetric oxa Michael additions with removable chirality information within the hydroxide source are reported. As enantiopure oxygen nucleophile functioning as chiral hydroxide equivalent N-formylnorephedrine (7) was used and conjugate additions to aliphatic (E)-nitro alkenes 2a-j were carned out in good yields (35-87%) and excellent diastereomeric excesses (de = 94-≥98%). After reduction of the nitro group and protection of the amino function (11a-h, 73-87%, both steps), the cleavage of the auxiliary occurred without epimerisation (69-99%) using Na/NH3. The Boc-protected 2-amino alcohols 12a-h could be obtained in good overall yields (30-58 %, four steps) and excellent diastereomeric and enantiomeric excesses (de, ee = 94-≥98%). Transition states explaining the overall stereochemical outcome are presented based on the absolute configuration determined by X-ray structure analysis on 8b.

Enantioselektive Synthese von vicinalen Aminoalkoholen durch Oxa-Michael-Addition

Keywords: Aminoalkohole; Asymmetrische Synthesen; Michael-Additionen; Nitroalkene; Synthesemethoden