1016669-67-2

Basic information

• Product Name: ((1R,2R)-2-Methoxycarbonylamino-cyclohexyl)-carbamic acid methyl ester
• Synonyms: ((1R,2R)-2-Methoxycarbonylamino-cyclohexyl)-carbamic acid methyl ester
• CAS NO: 1016669-67-2
• Molecular Weight: 230.264
• Mol File: 1016669-67-2.mol

Chemical Properties

• CAS DataBase Reference: ((1R,2R)-2-Methoxycarbonylamino-cyclohexyl)-carbamic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: ((1R,2R)-2-Methoxycarbonylamino-cyclohexyl)-carbamic acid methyl ester(1016669-67-2)
• EPA Substance Registry System: ((1R,2R)-2-Methoxycarbonylamino-cyclohexyl)-carbamic acid methyl ester(1016669-67-2)

Safety Data

• Hazardous Substances Data: 1016669-67-2(Hazardous Substances Data)

Upstream product

• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 79-22-1 methyl chloroformate 
• 32044-22-7 (1R,2R)-1,2-diaminocyclohexane tartrate 

Downstream Products

• 68737-65-5 (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane 

Relevant articles and documents

A new sparteine surrogate for asymmetric deprotonation of N-Boc pyrrolidine

(Chemical Equation Presented) The s-BuLi complex of a cyclohexane-derived diamine is as efficient as s-BuLi/(-)-sparteine for the asymmetric deprotonation of N-Boc pyrrolidine. This is the first example of high enantioselectivity using a non-sparteine-like diamine in such reactions. The ( S, S)-diamine is a useful (+)-sparteine surrogate and was utilized in short syntheses of (-)-indolizidine 167B and an intermediate for the synthesis of the CCK antagonist (+)-RP 66803.

Synthesis, resolution, and application of 2,2′-bis(diphenylphosphino) -3,3′-binaphtho[b]furan (BINAPFu)

(±)-2,2′-Bis(diphenylphosphino)-3,3′-binaphtho[2,1-b] furan (BINAPFu) was synthesized from 2-naphthoxyacetic acid in a five-step sequence in 62% overall yield. A variety of reported resolution procedures for biaryl bisphosphines did not work with (±)-BINAPFu; thus, a new resolution method was developed, involving the Staudinger reaction of the aforementioned racemate of BINAPFu with an enantiopure camphor sulfonyl azide derivative. The resulting diastereomeric phosphinimines were separated by flash chromatography. Subsequent hydrolysis to the corresponding bis-phosphine oxide and trichlorosilane reduction provided enantiopure BINAPFu. The absolute stereochemical configuration of BINAPFu was established by X-ray crystallography. BINAPFu was compared with commercially available 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP) in Pd(0)-catalyzed intermolecular Heck reactions. Investigation of the Heck arylation of 2,3-dihydrofuran showed BINAPFu to be more efficacious than BINAP in dioxane at 30°C. A variety of phosphorus selenides were prepared, and the 1JP-Se coupling constants measured, to obtain a comparative scale of parent phosphine basicity. The phosphorus atoms in BINAPFu were found to be electron deficient when compared with BINAP but slightly more electron rich than trifurylphosphine.