82769-76-4

Basic information

• Product Name: (S)-3-Amino-3-phenylpropan-1-ol
• Synonyms: (S)-3-AMINO-3-PHENYLPROPAN-1-OL;(S)-1-PHENYL-3-PROPANOLAMINE;(S)-BETA-PHENYLALANINOL;(S)-3-Amino-3-phenylpropan-1-ol(e.e.);(S)-3-Amino-3-phenylpropan-1-ol, 98% ee, 95%;(S)-3-PHENYL-BETA-ALANINOL ;(S)-3-Amino-3-phenylpropanol;(S)-3-Amino-3-phenylpropan-1-ol, 95%, ee:98%
• CAS NO: 82769-76-4
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21
• EINECS: 1312995-182-4
• Product Categories: Alcohol Aldehyde & acid series
• Mol File: 82769-76-4.mol

Chemical Properties

• Melting Point: 68-69 °C
• Boiling Point: 273.23°C (rough estimate)
• Flash Point: 131 °C
• Appearance: Colorless or white/Viscous Liquid or Low Melting Solid
• Density: 1.0406 (rough estimate)
• Vapor Pressure: 9.47E-05mmHg at 25°C
• Refractive Index: 1.4755 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 14.90±0.10(Predicted)
• CAS DataBase Reference: (S)-3-Amino-3-phenylpropan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Amino-3-phenylpropan-1-ol(82769-76-4)
• EPA Substance Registry System: (S)-3-Amino-3-phenylpropan-1-ol(82769-76-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 45-36/37/39-26
• RIDADR: 3259
• HazardClass: 8
• PackingGroup: Ⅲ
• Hazardous Substances Data: 82769-76-4(Hazardous Substances Data)

Usage

Chemical Properties

colorless viscous liquid or

Uses

(S)-3-Amino-3-phenylpropan-1-ol is a useful intermediate for the synthesis of dapoxetine.

InChI:InChI=1/C9H13NO.ClH/c10-9(6-7-11)8-4-2-1-3-5-8;/h1-5,9,11H,6-7,10H2;1H/t9-;/m0./s1

Upstream product

• 6335-76-8 3-amino-3-phenylpropionic acid ethyl ester 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 281681-23-0 1-acetoxy-3-acetylamino-3-phenylpropane 
• 86260-84-6 5-ethoxy-3-phenyl-4,5-dihydroisoxazole 
• 14397-33-2 3-phenyl-2-isoxazoline 
• 98748-93-7 3-trimethylsiloxy-1-phenylpropyl isocyanide 
• 81548-17-6 N-(3-hydroxy-1-phenylpropyl)acetamide 
• 81548-21-2 2-vinyl-4-phenyl-4H-5,6-dihydro-1,3-oxazine 
• 772-00-9 4-phenyl-1,3-dioxane 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 14898-52-3 methyl 3-amino-3-phenylpropanoate 
• 5650-41-9 3-hydroxy-1-phenylpropan-1-one 
• 4436-23-1 2-phenyloxetane 
• 81548-15-4 2-Methyl-4-phenyl-5,6-dihydro-4H-[1,3]oxazine 

Downstream Products

• 102877-48-5 3-amino-3-phenyl-propionaldehyde 
• 903635-44-9 trans-4-phenylcyclophosphamide 
• 68208-27-5 (2RS,4SR)-2--4-phenyl-2H-1,3,2-oxazaphosphorinane 2-oxide 
• 292140-03-5 (+/-)-2-[2-(diphenylphosphino)phenyl]-5,6-dihydro-4-phenyl-4H-1,3-oxazine 
• 281681-23-0 1-acetoxy-3-acetylamino-3-phenylpropane 
• 499193-75-8 3-[N-(2-bromo-3-methyl-2-butenyl)amino]-3-phenylpropan-1-ol 
• 499193-70-3 3-[N-(2-bromo-2-propenyl)amino]-3-phenylpropan-1-ol 
• 218449-48-0 (3-hydroxy-1-phenylpropyl)carbamate tert-butyl ester 
• 82769-75-3 (S)-(+)-3-(dimethylamino)-3-phenyl-1-propanol 
• 81548-17-6 N-(3-hydroxy-1-phenylpropyl)acetamide 
• 888298-12-2 3-amino-O-tert-butyldimethylsilyl-3-phenylpropan-1-ol 

Relevant articles and documents

Synthesis method of dapoxetine

The present invention provides a synthesis method of dapoxetine, comprising the following steps: S1, the (s)-3-amino-3-phenylpropionic acid or ester compounds dispersed in a solvent, reflux reaction under the action of a reducing agent, to give (s) - amino-3-phenylpropanol; S2, the (s) - amino-3-phenylpropanol dissolved in aqueous solution of carboxylic acid, added paraformaldehyde to warm up the reaction, to give (s) -3-dimethylamino-3-phenylpropanol; S3, (s)-3-Dimethylamino-3-phenylpropanol was dissolved in a solvent, protected by nitrogen, and reacted in a solution of alkali added dropwise at a higher temperature, and then 1-fluoronaphthalene was added to produce Williamson etherization reaction, to give (s)-N, N-dimethyl-3-(1-naphthooxy) amphetamine, i.e., dapoxetine. The synthesis method of dapoxetine of the present invention is inexpensive and easy to obtain raw materials, does not use toxic and dangerous reagents, will not react to the phenomenon of aggregation spray, the process is simple, suitable for industrial production.

Method for preparing amino alcohol compound by using halogenated intermediate

The invention discloses a method for preparing an amino alcohol compound by utilizing a halogenated intermediate. According to the method, an oxygen-halogen bond can be prepared by utilizing cyclic diacyl peroxide and halogenated salt under an illumination condition, and the oxygen-halogen bond is prone to homolysis under an illumination condition to form an active free radical, so the amino alcohol is finally prepared. The novel method for synthesizing the amino alcohol is high in atom utilization rate, simple in synthesis method and high in yield, so the consumption of halide for reactions with synthesis values is reduced, and the purposes of environmental protection and green chemistry are better achieved.

Site-Specific C(sp3)–H Aminations of Imidates and Amidines Enabled by Covalently Tethered Distonic Radical Anions

The utilization of N-centered radicals to synthesize nitrogen-containing compounds has attracted considerable attention recently, due to their powerful reactivities and the concomitant construction of C?N bonds. However, the generation and control of N-centered radicals remain particularly challenging. We report a tethering strategy using SOMO-HOMO-converted distonic radical anions for the site-specific aminations of imidates and amidines with aid of the non-covalent interaction. This reaction features a remarkably broad substrate scope and also enables the late-stage functionalization of bioactive molecules. Furthermore, the reaction mechanism is thoroughly investigated through kinetic studies, Raman spectroscopy, electron paramagnetic resonance spectroscopy, and density functional theory calculations, revealing that the aminations likely involve direct homolytic cleavage of N?H bonds and subsequently controllable 1,5 or 1,6 hydrogen atom transfer.

Base-induced Sommelet–Hauser rearrangement of N-(α-(2-oxyethyl)branched)benzylic glycine ester-derived ammonium salts via a chelated intermediate

The base-induced Sommelet–Hauser (S–H) rearrangement of N-(α-branched)benzylic glycine ester-derived ammonium salts 1 was investigated. When the α-branched substituent was a simple alkyl, such as a methyl or butyl, desired S–H rearrangement product 2 was obtained in low yield with formation of the [1,2] Stevens rearranged 4 and Hofmann eliminated products 5 and 6. However, when the α-branched substituent had a 2-oxy moiety, such as 2-acetoxyethyl or 2-benzoyloxyethyl, the yields of 2 were improved. These results could be explained by formation of chelated intermediate C that stabilizes the carbanionic ylide, and the subsequent initial dearomative [2,3] sigmatropic rearrangement would be accelerated. The existence of C was supported by mechanistic experiments. This enhancement effect is not very strong or effective; however, it will expand the synthetic usefulness of ammonium ylide rearrangements.

Synthetic method of dapoxetine and intermediate thereof

The invention discloses a synthetic method of dapoxetine and its intermediate, i.e., (S)-3-(tert-butyloxycarbonyl)amino-3-phenylpropanol as shown in a formula 5 which is described in the specification. The synthetic method of (S)-3-(tert-butyloxycarbonyl)amino-3-phenylpropanol is as shown in a synthesis route which is described in the specification, wherein a compound 3 and acetaldehyde are subjected to a Mannich reaction in an organic solvent under the action of a supramolecular catalyst constructed by a chiral catalyst and a polymer so as to obtain a compound 4, and the polymer is at least one selected from of the group consisting of PEG 200, PEG 400, PEG 600, MeOPEG 750, PEG 800, PEG 1000, PPG 800 and PPG 1000. The dapoxetine is synthesized from the (S)-3-(tert-butyloxycarbonyl)amino-3-phenylpropanol prepared by using the above method according to steps as shown in the synthesis route. The synthetic method of dapoxetine and the intermediate thereof has the characteristics of usage of cheap and easily available raw materials, high yield and low cost, and is more beneficial to industrial production.

Lipophilic NHC assisted one-pot synthesis of syncarpamide analogues in aqueous medium

Lipophilic NHC catalysis in aqueous medium was reported for the synthesis of biologically relevant (a)symmetrically substituted and unsymmetrically substituted syncarpamide analogues. All the reported reactions were performed in the absence of any expensive metal salts or additives. A diverse array of syncarpamide analogues was obtained in good yields. Lipophilic NHC catalysis was also extended to chemoselective transesterification reactions.

COMPOUNDS AND USES THEREOF

The present invention features compounds useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.

Preparation method of 3-aminopropanol or 3-aminopropionic acid derivative

The invention provides a preparation method of an optically active 3-aminopropanol or 3-aminopropionic acid derivative, and belongs to the technical field of organic synthesis. A compound having a structure as shown in a formula II and a formula III is used as a raw material, and the optically active 3-aminopropanol or 3-aminopropionic acid derivative is obtained through four basic steps, namely dehydration condensation, hydrogenation reduction, reduction and hydrolysis. The raw materials adopted in the preparation method are easy to obtain and low in cost; as a chiral phosphine-transitional metal catalyst is used in the hydrogenation reduction reaction, the optically active 3-aminopropanol or 3-aminopropionic acid derivative is efficient, high in selectivity, low in cost and suitable forlarge-scale production. Compared with existing chemical resolution and chiral introduction, the asymmetric hydrogenation synthesis method provided by the invention only produces one chiral product, ishigh in yield, and has relatively high advantages in economy and raw material utilization rate.

5-hydroxytryptamine re-absorption inhibitor crystal form and preparation method thereof

The invention relates to a dapoxetine hydrochloride crystal form and a preparation method thereof, and belongs to the technical field of drug synthesis. The preparation method comprises: dissolving (S)-3-amino-3-phenylpropionic acid in an appropriate solvent, adding a reducing agent and a Lewis acid, and reducing to obtain (S)-3-amino-3-phenylpropanol; dissolving the (S)-3-amino-3-phenylpropanolin formic acid, and adding formaldehyde to produce (S)-3-dimethylamino-3-phenylpropanol; dissolving the (S)-3-dimethylamino-3-phenylpropanol in an organic solvent, adding an alkali and 1-fluoronaphthalene, carrying out heating stirring for 5-10 h, adding water and an organic solvent, extracting, carrying out spin drying on the organic phase, dissolving with a solvent, adding concentrated hydrochloric acid in a dropwise manner, and carrying out pressure reducing distillation to remove the solvent and the water; and re-crystallizing with a suitable solvent to obtain the dapoxetine hydrochloride.According to the present invention, the Cu-Ka radiation results of the obtained dapoxetine hydrochloride crystal form show that the characteristic peaks represented by 2[theta] angle are positioned at 6.24+/-0.2, 15.03+/-0.2, 18.87+/-0.2, 20.63+/-0.2 and 25.28+/-0.2 in the X-ray powder diffraction pattern.

Synthesis, separation-purification, and salt forming method of dapoxetine

The invention provides a novel synthesis, gradient separation-purification, and salt forming method of dapoxetine. Easily available and cheap benzaldehyde is taken as the primary raw material of the synthesis route. The whole reaction conditions are mild. The synthesis route is short. No highly toxic or explosive raw material is used. The problem of chiral separation is well solved in the route. During the separation process, the product is purified. Finally, chlorinated hydromethyl tert-butyl ether which does not have any side or toxic effect is used to carry out salt forming. A large amount of labor, material, and time is saved. The production cost is reduced. The synthesis does not need any special equipment. The operation is simple and convenient. The method has a good industrial application prospect.