On October 12, 2000, Matsubara, Koki; Kida, Hitoshi published a patent.HPLC of Formula: 167316-28-1 The title of the patent was Method for the preparation of tricyclic amino alcohol derivatives through azides. And the patent contained the following:
Tricyclic amino alc. derivatives represented by general formula [I; wherein R1 is lower alkyl or benzyl; *1 represents an asym. carbon atom; R2 is hydrogen, halogeno or hydroxyl; and A is a substituent represented by general formula Q or Q1 (wherein X is NH, O, or S; R5 is hydrogen, hydroxyl, amino, or acetylamino; and *2 represents an asym. carbon atom when R5 is not hydrogen)] are prepared via asym. reduction of phenacyl azides (II; R21 is hydrogen, halogeno or (un)protected hydroxyl; R3 is hydrogen or amino-protecting group; and R1 is lower alkyl or benzyl) to chiral azido alcs. (III) or amino alcs. (IV; R21, R1, R3 are same as above). This process makes it possible to prepare the derivatives I by a short, easy, inexpensive, and practical production process excellent in industrial workability. Compounds I are useful in the treatment and prevention of diabetes, obesity, hyperlipidemia, and so on (no data). Thus, 58 mg [(S,S)-N-methanesulfonyl-1,2-diphenylethylenediamine](p-cymene)ruthenium (preparation given) was added to a solution of 3.6 g 2-azido-1-(4-benzyloxy-3-methylsulfonylaminophenyl)ethanone (preparation given) in 2.5 mL formic acid/triethylamine solution (Fluka) in 6.5 mL THF and stirred at 5° for 43 h to give 95.0% (R)-2-azido-1-(4-benzyloxy-3-methylsulfonylaminophenyl)ethanol (94.2 %e.e.). In another example, 2-amino-1-(4-benzyloxy-3-methylsulfonylaminophenyl)ethanone hydrochloride (1.0 g) and 2 μL Et3N were added to a solution of 133 mg chloro(1,5-cyclooctadiene)rhodium(II) dimer and 397 mg (2R,4R)-N-(tert-butoxycarbonyl)-4-dicyclohexylphosphino-2-diphenylphosphinopyrrolidine and stirred under hydrogen atm. at room temperature for 24 h to give 94.0% (R)-2-amino-1-(4-benzyloxy-3-methylsulfonylaminophenyl)ethanol (V). Reductive benzylation of V with benzaldehyde in the presence of Pt2O under hydrogen atm. at room temperature for 15 h followed by amidation with (9H-carbazol-2-yloxy)acetic acid using DCC in THF at room temperature for 24 h, borane reduction in THF, and hydrogenolysis over 10% Pd-C in MeOH gave (R)-2-[N-[2-(9H-carbazol-2-yloxy)]ethyl]amino-1-(4-hydroxy-3-methylsulfonylaminophenyl)ethanol. The experimental process involved the reaction of N-[(1S,2S)-2-Amino-1,2-diphenylethyl]-1,1,1-trifluoromethanesulfonamide(cas: 167316-28-1).HPLC of Formula: 167316-28-1
The Article related to tricyclic amino alc preparation treatment diabetes obesity hyperlipidemia, asym reduction phenacyl azide, ruthenium complex asym reduction catalyst, carbazolyloxyethylaminophenylethanol preparation antidiabetic, phenylethanolamine carbazolyloxyethyl preparation antidiabetic and other aspects.HPLC of Formula: 167316-28-1
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics