26652-09-5

Basic information

• Product Name: RITODRINE
• Synonyms: 4-hydroxy-alpha-(1-((2-(4-hydroxyphenyl)ethyl)amino)ethyl)-benzenemethano(;4-hydroxy-alpha-(1-((2-(4-hydroxyphenyl)ethyl)amino)ethyl)benzenemethanol(r*;erythro-p-hydroxy-alpha-(1-((p-hydroxyphenethyl)amino)ethyl)benzylalcohol;p-hydroxy-alpha-(1-((p-hydroxyphenethyl)amino)ethyl)-benzylalcohoerythr;ritodrina;RITODRINE;Benzenemethanol, 4-hydroxy-a-[(1R)-1-[[2-(4-hydroxyphenyl)ethyl]amino]ethyl]-, (aS)-rel- (9CI);Benzenemethanol, 4-hydroxy-a-[1-[[2-(4-hydroxyphenyl)ethyl]amino]ethyl]-, (R*,S*)-
• CAS NO: 26652-09-5
• Molecular Formula: C17H21NO3
• Molecular Weight: 287.35
• EINECS: 247-879-9
• Mol File: 26652-09-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 512.3 °C at 760 mmHg
• Flash Point: 175.6 °C
• Appearance: /
• Density: 1.213 g/cm³
• Vapor Pressure: 2.55E-11mmHg at 25°C
• Refractive Index: 1.618
• PKA: pKa 9.0 (Uncertain)
• CAS DataBase Reference: RITODRINE(CAS DataBase Reference)
• NIST Chemistry Reference: RITODRINE(26652-09-5)
• EPA Substance Registry System: RITODRINE(26652-09-5)

Safety Data

• Hazardous Substances Data: 26652-09-5(Hazardous Substances Data)

Usage

Description

Ritodrine, 4-hydroxy-α-[1-[(4′-hydroxyphenethyl)amino]ethyl]benzylic alcohol (11.1.19), differs slightly from epinephrine, and in the given example only one hydroxyl group has been added to the aromatic ring of the phenylethylamino region of classic sympathomimetics. The second major difference between the examined series is the replacement of the traditionally terminal iso-propyl or tert-butylamine region with a p-hydroxyphenylethylamine. Finally, the third difference is the presence of a methyl group at the α-atom of the phenylethylamine region of sympathomimetics, which makes it similar to isoetharine.

Uses

Different sources of media describe the Uses of 26652-09-5 differently. You can refer to the following data:
1. Relaxant (smooth muscle).
2. Ritodrine is a selective β2-adrenoreceptor stimulant, predominantly of the urino-genital system. It is used as a tocolytic agent for problems associated with premature miscarriages, and only in specialized medical facilities.

General Description

Ritodrine is a selective β2-agonist that wasdeveloped specifically for use as a uterine relaxant. Its uterineinhibitory effects are more sustained than its effects onthe cardiovascular system, which are minimal comparedwith those caused by nonselective β-agonists. The cardiovasculareffects usually associated with its administrationare mild tachycardia and slight diastolic pressure decrease.Usually, it is administered initially by intravenous infusionto stop premature labor and subsequently it may be givenorally.

Clinical Use

Ritodrine is a selective β2-agonist that is used exclusively for relaxing uterine muscle and inhibiting the contractions of premature labor. Terbutaline, in addition to its use as a bronchodilator, also has been used for halting the contractions of premature labor.

Synthesis

Ritodrine is synthesized from 4-benzyloxypropiophenone, which undergoes bromination into 4-benzyloxy-α-bromopropiophenone (11.1.17). This is reacted with 2-(4-benzyloxyphenyl)ethylamine, forming an intermediate product (11.1.18), which undergoes further debenzylation by hydrogen using a palladium catalyst, giving ritodrine (11.1.19) [24,25].

InChI:InChI=1/C17H21NO3/c1-12(17(21)14-4-8-16(20)9-5-14)18-11-10-13-2-6-15(19)7-3-13/h2-9,12,17-21H,10-11H2,1H3/t12-,17-/m0/s1

Upstream product

• 1104584-63-5 (1R,2S)-1-(4-benzyloxyphenyl)-2-[2-(4-benzyloxyphenyl)ethyl]amino-1-propanol 
• 21086-33-9 2-bromo-1-(4-methoxyphenyl)-1-propanone 
• 121-97-1 4-Methoxypropiophenone 
• 79-24-3 Nitroethane 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 40167-10-0 2-[4-(benzyloxy)phenyl]acetaldehyde 

Relevant articles and documents

Preparation method for high purity ritodrine hydrochloride

The invention provides a preparation method for erythro form ritodrine hydrochloride shown as formula I. The method includes: subjecting a compound II and a bromination reagent to alpha bromination reaction to obtain a compound III, then conducting nucleophilic substitution with a compound IV to synthesize a compound V, performing deprotection to generate (1-(4-hydroxyphenyl)-2-[2-(4-hydroxyphenyl)ethylamino]propyl-1-one (VI), and then conducting reduction synthesis of ritodrine, performing splitting, and finally adding hydrochloric acid to form ritodrine hydrochloride. The method provided by the invention can significantly reduce the isomer impurity D, and can achieve efficient preparation of the medicinal purity product.

Catalytic asymmetric synthesis of (-)-ritodrine hydrochloride via silyl enol ether amination using dirhodium(II) tetrakis [tetrafluorophaloyl-(S)-tert-leucinate]

A catalytic asymmetric synthesis of (-)-ritodrine hydrochloride was achieved, incorporating an enantioselective amination of (Z)-silyl enol ether derived from 4-benzyloxypropiophenone with [(2-nitrophenylsulfonyl)imino]phenyliodinane (NsN=IPh) and a chelation-controlled reduction of the ketone carbonyl group with Zn(BH4)2 as the key steps. The use of dirhodium(II) tetrakis[tetrafluorophthaloyl-(S)-tert-leucinate] as a catalyst produced the targeted α-amino ketone in 94% yield with 91% ee.

Synthesis of β phenylethylamine derivatives. X. N (hydroxy and methoxy aralkyl) derivatives

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