61477-40-5 Usage
Description
(R)-3-AMINO-1-BUTANOL, also known as (R)-α-amino-1-butanol, is an alcohol organic compound characterized by its chiral center. It is a colorless liquid and serves as a crucial intermediate in the synthesis of various chiral drugs, making it a significant component in the pharmaceutical industry.
Uses
Used in Pharmaceutical Industry:
(R)-3-AMINO-1-BUTANOL is used as a key intermediate for the synthesis of chiral drugs for various medical applications. Its chiral nature allows for the creation of drugs with specific therapeutic effects, targeting different receptors and pathways in the body.
Used in Drug Development:
(R)-3-AMINO-1-BUTANOL is utilized in drug development as a building block for designing and creating novel pharmaceutical compounds. Its versatility in chemical reactions enables the development of new drugs with improved efficacy, safety, and selectivity.
Used in Chiral Synthesis:
In the field of chiral synthesis, (R)-3-AMINO-1-BUTANOL is used as a starting material for the production of enantiomerically pure compounds. This is essential for creating drugs with desired pharmacological properties, as the stereochemistry of a molecule can significantly impact its biological activity.
Used in Research and Development:
(R)-3-AMINO-1-BUTANOL is also employed in research and development laboratories for studying the effects of chirality on drug action, metabolism, and toxicity. This helps in understanding the role of stereochemistry in drug design and development, leading to more effective and safer medications.
Synthesis
Release of (R)-3-amino-1-butanol From the (S)-mandelic Salt Thereof; The (S)-mandelic salt of (R)-3-amino-1-butanol obtained in Example 1.1 (372 g, 1.54 mol) was suspended in triethanolamine (1 I) at 80° C., and the slurry was admixed with sodium methoxide (277.6 g, 1.54 mol; 30% in methanol), which gave a clear solution. This was heated to 100° C. and vacuum was applied. In a stepwise manner, a pressure of 750, 500, 250, 100, 50 and finally 20 mbar was applied. Through an attached Claisen distillation head (no return stream, no column), a clear distillate distilled over at a top temperature of 50 to 60° C., which was predominantly methanol. The pressure was then lowered further to 5 mbar, and (R)-3-amino-1-butanol distilled over at a top temperature of 76° C. The product was distilled once again in a water jet pump vacuum, in the course of which (R)-3-amino-1-butanol distilled over at 93° C. and 26 mbar. This gave 125 g (91% of theory) of (R)-3-amino-1-butanol as a colorless liquid with an optical purity of 99.6% ee.The optical purity of (R)-3-amino-1-butanol was determined by means of GC. To this end, (R)-3-amino-1-butanol (200 mg) and triethylamine (300 mg) were dissolved in diethyl ether (15 ml) and admixed with trifluoroacetic anhydride (0.6 ml). After stirring for 30 minutes, saturated ammonium chloride solution (5 ml) was added and the mixture was stirred for a further 15 minutes. Subsequently, the mixture was left to stand until two phases had formed, and a sample of the upper clear phase was analyzed by GC.Column: Hydrodex-TBDAc, 25 m×0.25 mm, Macherey & NagelInlet temperature: 250° C.Detector temperature: 250° C.Injection volume : 0.5 μlMode: SplitSplit ratio: 100:1Carrier gas: HeFlow: 0.8 ml/min (constant flow)Program:Initial temperature: 135° C.Initial time: 10 minRate: 5° C./minFinal temperature: 170° C.Final time: 35 minRetention times:R enantiomer: 17.68 min (N-trifluoroacylated) 21.23 min (N,O-bis-trifluoroacylated)S enantiomer: 18.24 min (N-trifluoroacylated) 20.11 min (N,O-bis-trifluoroacylated)
Check Digit Verification of cas no
The CAS Registry Mumber 61477-40-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,1,4,7 and 7 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 61477-40:
(7*6)+(6*1)+(5*4)+(4*7)+(3*7)+(2*4)+(1*0)=125
125 % 10 = 5
So 61477-40-5 is a valid CAS Registry Number.
61477-40-5Relevant articles and documents
Triazole derivative with tumor cell calcium ion channel and preparation method and application thereof
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Paragraph 0126-0131, (2021/10/27)
The invention relates to the technical field of pharmaceutical chemistry synthesis, in particular to a triazole derivative with a tumor cell calcium ion channel and a preparation method and application thereof. By click reaction, benzyl in the structure is changed to 1, 2 and 3 - triazole structures to obtain a novel compound, can inhibit growth of tumor cells by influencing calcium ion channels in tumor cells, and has remarkable application value.
Preparation method of (R)-3-aminobutanol
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Paragraph 0065-0072, (2021/09/04)
The invention provides a preparation method of (R)-3-aminobutanol. The method specifically comprises the following steps: carrying out reduction reaction on a reducing agent and (R)-3-aminobutyric acid, and carrying out post-treatment to obtain (R)-3-aminobutanol, wherein the reducing agent is zinc borohydride. According to the method disclosed by the invention, the risk of reduction reaction is remarkably reduced, so that the process is safer and more controllable, and large-scale production is easy to realize.
Data mining of amine dehydrogenases for the synthesis of enantiopure amino alcohols
Guo, Jinggong,Li, Jun-Kuan,Ma, Jun-An,Miao, Yuchen,Qu, Ge,Sun, Zhoutong,Wang, Hongyue
, p. 5945 - 5952 (2020/10/08)
Chiral amino alcohols are essential building blocks for the pharmaceutical industry, and are widely present in natural and synthetic bioactive compounds. Amine dehydrogenases (AmDHs) can asymmetrically reduce prochiral ketones with low-cost ammonia to chiral amines and water as by-products, using NAD(P)H as a cofactor under mild conditions, but hydroxy ketones with formation of chiral hydroxy amines have rarely been investigated. In this study, six new bacterial AmDHs derived from amino acid dehydrogenases (AADHs) were identified by data mining, and five out of the six enzymes were able to efficiently reduce 1-hydroxybutan-2-one (1a) to (S)-2-aminobutan-1-ol ((S)-2a) with 19-99% conversions and 99% ee. The five AmDHs were purified and biochemically characterized for reductive amination activity towards substrate 1a with the optimal pH at 8.5 or 9.0 and the optimal temperature at 45 °C, 50 °C or 55 °C, and provided reductive amination of a broad range of prochiral α-hydroxy ketones, and even of a model β-hydroxy ketone leading to β-hydroxy amine with 99% ee. Our study expands the toolbox of AmDHs in the synthesis of chiral amino alcohols.