188690-83-7

Basic information

• Product Name: Formamide, N-[5-[(1R)-1-hydroxy-2-[[(1R)-1-methyl-2-(4-methoxyphenyl)ethyl](phenyl methyl)amino]ethyl]-2-(phenylmethoxy)phenyl]-
• CAS NO: 188690-83-7
• Molecular Formula: C33H36N2O4
• Molecular Weight: 524.66
• Mol File: 188690-83-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Formamide, N-[5-[(1R)-1-hydroxy-2-[[(1R)-1-methyl-2-(4-methoxyphenyl)ethyl](phenyl methyl)amino]ethyl]-2-(phenylmethoxy)phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Formamide, N-[5-[(1R)-1-hydroxy-2-[[(1R)-1-methyl-2-(4-methoxyphenyl)ethyl](phenyl methyl)amino]ethyl]-2-(phenylmethoxy)phenyl]-(188690-83-7)
• EPA Substance Registry System: Formamide, N-[5-[(1R)-1-hydroxy-2-[[(1R)-1-methyl-2-(4-methoxyphenyl)ethyl](phenyl methyl)amino]ethyl]-2-(phenylmethoxy)phenyl]-(188690-83-7)

Safety Data

• Hazardous Substances Data: 188690-83-7(Hazardous Substances Data)

Upstream product

• 64-18-6 formic acid 
• 289657-26-7 (R,R)-3-amino-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenyl methyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol 
• 100-46-9 benzylamine 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 43229-65-8 [2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amine 
• 1096141-37-5 C₁₇H₁₉NO 
• 1049695-95-5 benzyl-[2-(4-methoxy-phenyl)-1-methyl-ethyl]-amine; hydrochloride 
• 1198769-18-4 (R)-4-benzyloxy-3-nitro-α-(N-benzyl-N-(1-methyl-2-p-methoxyphenylethyl)amino)acetophenone 
• 245759-64-2 (R)-N-benzyl-N-(1-methyl-2-p-methoxyphenylethyl)amine L-mandelate 
• 245759-64-2 N-benzyl-1-(4-methoxyphenyl)propan-2-amine mandalate salt 
• 201677-57-8 N-[2-(benzyloxy)-5-[(2R)-oxiran-2-yl]phenyl]formamide 
• 67346-60-5 (R)-(-)-1-(4'-methoxyphenyl)-2-benzylaminopropane 
• 201677-59-0 N-[5-((1R)-2-bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]carboxamide 
• 245759-65-3 (R,R)-3-nitro-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol 

Downstream Products

• 73573-87-2 (R,R)-formoterol 

Relevant articles and documents

Method for synthesizing arformoterol free alkali

The invention discloses a method for synthesizing arformoterol free alkali, which comprises the following steps of: (1) performing carbonyl chiral reduction reaction on a compound shown as a formula SM1 serving as a raw material in a first solvent to obtain a reaction solution containing a compound shown as a formula M1, and concentrating to dryness; (2) dissolving the material obtained in the step (1) with a second solvent, carrying out a hydrogenation reaction to obtain a reaction liquid containing a compound represented by a formula M2, filtering the reaction liquid, and cooling the filtrate; (3) carrying out formylation reaction on the filtrate cooled in the step (2) to obtain a reaction solution containing a compound as shown in a formula M3, and concentrating to dryness; (4) dissolving the material obtained in the step (3) with a third solvent, carrying out a cyclization reaction to obtain a reaction liquid containing a compound represented by a formula M4 and free SM2, filtering, and concentrating the filtrate to dryness; and (5) dissolving the material obtained in the step (4) with a fourth solvent, carrying out a condensation reaction to obtain an arformoterol precursor represented by a formula M5, and carrying out hydrogenation debenzylation on the M5 to obtain arformoterol.

PROCESSES FOR PREPARING SUBSTANTIALLY PURE ARFORMOTEROL AND ITS INTERMEDIATES

Provided herein are improved, convenient and industrially advantageous processes for the preparation of N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide (Arformoterol) or a pharmaceutically acceptable salt thereof, in high yield and purity. Provided further herein is an improved and industrially advantageous process for the preparation of a substantially enantiomerically pure arformoterol intermediate, (R)-4-methoxy-α-methyl-N-(phenylmethyl)benzeneethanamine.

Enantio- and diastereoselective synthesis of all four stereoisomers of formoterol

Enantioselective syntheses of all four stereoisomers of formoterol are accomplished using asymmetric catalytic borane reductions with chiral oxazaborolidines as reducing agents.