STEROIDS: PART II. 6-AMINO STEROIDS

1960 ◽  
Vol 38 (6) ◽  
pp. 981-986 ◽  
Author(s):  
Barbara G. Ketcheson ◽  
Alfred Taurins
Keyword(s):  
High Pressure ◽  
Acetic Acid ◽  
Acid Medium ◽  
Catalytic Hydrogenation ◽  
Acid Treatment ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Acetic Acid Medium ◽  
Propyl Alcohol

Reduction of methyl 3β-acetoxy-6-oximinodinorcholanate using sodium in n-propyl alcohol, and acetylation, gave 6α-acetamido-3β-acetoxydinorcholanic acid; treatment with lithium aluminum hydride in tetrahydrofuran provided 3β,22ξ-dihydroxydinorcholan-6-one. High-pressure hydrogenation of methyl 3β-acetoxy-6-nitro-5-dinorcholenate, using palladium black as catalyst in acetic acid medium, afforded methyl 6ξ-acetamido-3β-acetoxy-5α-dinorcholanate. Under identical conditions, catalytic hydrogenation of 3β-acetoxy-6-nitro-5-cholestene resulted in the formation of 6β-acetamido-3β-acetoxy-5α-cholestane and 6ξ-acetamido-3β-acetoxy-5β-cholestane.

PSEUDACONITINE, AND THE STEREOCHEMICAL RELATIONSHIP OF THE HIGHLY OXYGENATED ACONITE ALKALOIDS

1963 ◽  
Vol 41 (6) ◽  
pp. 1485-1489 ◽  
Author(s):  
Y. Tsuda ◽  
Léo Marion
Keyword(s):  
Acetic Acid ◽  
Absolute Configuration ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Reduction Product ◽  
Lithium Aluminum ◽  
Partial Hydrolysis ◽  
Previous Knowledge ◽  
Relationship Of ◽  
Hydrolysis Of

An alkaloid isolated from Aconitum spicatum Stapf has been found to be identical not only with the originally described pseudaconitine but also with 'α-pseudaconitine'. The product of the partial hydrolysis of the base, i.e., veratroylpseudaconine, is dextrorotatory, and not laevorotatory as recorded in the old literature. On heating, pseudaconitine undergoes pyrolysis, loses the elements of acetic acid, and gives rise to pyropseudaconitine. This substance, on treatment with lithium aluminum hydride, is converted to demethoxyisopyropseudaconine which is identical with the Wolff–Kishner reduction product of pyraconine. This correlation establishes that pseudaconitine and aconitine possess the same absolute configuration, which, in the light of previous knowledge, is extended also to indaconitine, delphinine, mesaconitine, and jesaconitine.

A simple synthesis of (±)-1,2,3,6-tetrahydro-2,3′-bipyridine (anatabine) and (±)-3-(2-piperidinyl)pyridine (anabasine) from lithium aluminum hydride and pyridine

1997 ◽  
Vol 75 (6) ◽  
pp. 616-620 ◽  
Author(s):  
Chi-Ming Yang ◽  
Dennis D. Tanner
Keyword(s):  
Catalytic Hydrogenation ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Simple Synthesis ◽  
Lithium Aluminum ◽  
Pyridine Solution ◽  
Hydrolysis Of

The hydrolysis of a pyridine solution of lithium tetrakis(N-dihydropyridyl)aluminate (LDPA), which was prepared at 0 °C, yields a mixture of 1,4-, 1,2-, and 2,5-dihydropyridines (DHPs) in a ratio of 26:37:38. The subsequent reversible base-catalyzed condensation of a 1:1 mixture of 1,2- and 2,5-DHPs carried out in the presence of oxygen affords an 89% yield of (±)-anatabine. When the reaction mixture is allowed to stand in the presence of oxygen, anabasine is slowly formed from anatabine by the reaction of the residual DHPs. Anatabine can also be converted into (±)-anabasine by catalytic hydrogenation. Keywords: lithium aluminum hydride, pyridine, anatabine, anabasine.

Derivatives of 2-pyrazolin-5-one. V. Preparation and properties of 1′,2′-dihydrospiro[[2]pyrazoline-4,3′ (4′H)-quinoline]-5-one.derivatives and related compounds

1977 ◽  
Vol 55 (15) ◽  
pp. 2856-2866 ◽  
Author(s):  
Ronald T. Coutts ◽  
Abdel-Monaem El-Hawari
Keyword(s):  
Acetic Acid ◽  
Sodium Borohydride ◽  
Lithium Aluminum Hydride ◽  
Catalytic Reduction ◽  
Aluminum Hydride ◽  
Spiro Compounds ◽  
Lithium Aluminum ◽  
Aldehydes And Ketones ◽  
Derivatives Of ◽  
Related Compounds

1′,2′-Dihydro-3-methyl-1-phenylspiro[[2]pyrazoline-4,3′(4′H)-quinoline]-5-one (8q), the structurally related 1,3-diphenylspiro[pyrazolone-quinoline] 8r and numerous 2′-substituted derivatives of 8q and 8r are readily accessible from catalytic reduction of 3-methyl-1-phenyl- or 1,3-diphenyl-4-(2-nitrobenzyl)-2-pyrazolin-5-one (1a, 1b, respectively) in alcohols (with the incorporation of the alkylidene moiety) or by interaction of the corresponding 2-aminobenzyl precursors (3a, 3b) with appropriate aldehydes and ketones. All spiro compounds were characterized by mass, ir, and 1Hmr spectra. The products obtained by reducing the spiro compounds with sodium borohydride and with lithium aluminum hydride are described. Reduction of 1a and 1b with zinc and acetic acid gave 3-methyl-1-phenyl- and 1,3-diphenyl-1H-pyrazolo[3,4-b]quinoline (2a, 2b, respectively).

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