117160-99-3

Usage

Uses

Used in the synthesis of renin inhibitors.

InChI:InChI=1/C9H19NO.ClH/c10-9(7-11)6-8-4-2-1-3-5-8;/h8-9,11H,1-7,10H2;1H/t9-;/m0./s1

Upstream product

• 3182-95-4 L-Phenylalaninol 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 103322-56-1 tert-butyl [(1S)-2-cyclohexyl-1-(hydroxymethyl)ethyl]carbamate 
• 63-91-2 L-phenylalanine 
• 98105-41-0 methyl S-3-cyclohexyl-2-(t-butoxycarbonylamino)propionate 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 

Downstream Products

• 1021495-50-0 (S)-2-(cyclohexylmethyl)-1-(4-nitrobenzenesulfonyl)aziridine 
• 1093865-10-1 1,1-dimethylethyl [(1S)-2-azido-1-(cyclohexylmethyl)ethyl]methylcarbamate 
• 884511-41-5 (S)-tert-butyl (1-amino-3-cyclohexylpropan-2-yl)(methyl)carbamate 
• 884511-11-9 (S)-tert-butyl (1-azido-3-cyclohexylpropan-2-yl)carbamate 
• 1073338-60-9 (5S)-5-(cyclohexylmethyl)morpholin-3-one 
• 113828-85-6 Cbz-3-cyclohexyl-L-alaninol 
• 1085529-18-5 (2S)-3-cyclohexyl-2-{[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]amino}propan-1-ol 
• 1073338-59-6 2-chloro-N-[(1S)-2-cyclohexyl-1-(hydroxymethyl)ethyl]acetamide 
• 1039046-88-2 C₂₁H₂₄N₂O 

Relevant academic research and scientific papers

Reductions of aromatic amino acids and derivatives

Catalytic reduction of phenylalanine and phenylglycine derivatives can be achieved with rhodium on carbon or alumina to give good yields of the corresponding cyclohexyl derivatives. The procedure can be scaled.

Catalytic Hydrogenation of Chiral α-Amino and α-Hydroxy Esters at Room Temperature with Nishimura Catalyst without Racemization

The hydrogenation of carboxylic acid derivatives at room temperature was investigated. With a mixed Rh/Pt oxide (Nishimura catalyst), low to medium activity was observed for various α-amino and α-hydroxy esters. At 100 bar hydrogen pressure and 10% catalysts loading, high yields of the desired amino alcohols and diols were obtained without racemization. The most suitable α-substituents were NH2, NHR, and OH, whereas β-NH2 were less effective. Usually, aromatic rings were also hydrogenated, but with the free bases of amino acids as substrates, some selectivity was observed. No reaction was found for α-NR2, α-OR, and unfunctionalized esters; acids and amides were also not reduced under these conditions. A working hypothesis for the mode of action of the catalyst is presented.

Probes of the Active Site of Norepinephrine N-Methyltransferase: Effect of Hydrophobic and Hydrophilic Interactions on Side-Chain Binding of Amphetamine and α-Methylbenzylamine

A series of ω-substituted analogues of amphetamine and α-methylbenzylamine were prepared and evaluated as inhibitors of norepinephrine N-methyltransferase (NMT).These included several alkyl side chain extended analogues (1-5), as well as the terminally hydroxylated derivatives phenylalanol (6a) and Phenylglycinol (7a).None of the alkyl-substituted derivatives displayed appreciable activity as inhibitors; however, the hydroxylated analogues were up to twofold more potent than the parent compounds.The positive contribution of the side-chain hydroxy suggests that theterminal methyl group of the lead compounds is situated close to a hydrophilic area or hydrogen bonding functional group within the active site.