123366-90-5

Basic information

• Product Name: (S)-3-phenyl-2-(1H-pyrrol-1-yl)propan-1-ol
• Synonyms: (S)-3-phenyl-2-(1H-pyrrol-1-yl)propan-1-ol
• CAS NO: 123366-90-5
• Molecular Weight: 201.268
• Mol File: 123366-90-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S)-3-phenyl-2-(1H-pyrrol-1-yl)propan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-phenyl-2-(1H-pyrrol-1-yl)propan-1-ol(123366-90-5)
• EPA Substance Registry System: (S)-3-phenyl-2-(1H-pyrrol-1-yl)propan-1-ol(123366-90-5)

Safety Data

• Hazardous Substances Data: 123366-90-5(Hazardous Substances Data)

Upstream product

• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 3182-95-4 L-Phenylalaninol 
• 46687-57-4 (S)-3-phenyl-2-(1H-pyrrol-1-yl)propanoic acid 
• 116763-08-7 methyl (S)-3-phenyl-2-(1H-pyrrol-1-yl)propanoate 

Downstream Products

• 3182-95-4 L-Phenylalaninol 

Relevant articles and documents

Pyrrole-Protected β-Aminoalkylzinc Reagents for the Enantioselective Synthesis of Amino-Derivatives

Chiral β-aminoalkylzinc halides were prepared starting from optically pure commercial β-amino-alcohols. These amino-alcohols were converted to the corresponding N-pyrrolyl-protected alkyl iodides which undergo a zinc insertion in the presence of LiCl (THF, 25 °C, 10–90 min). Subsequent Negishi cross-coupling or acylation reactions with acid chlorides produced amino-derivatives with retention of chirality. Diastereoselective CBS-reductions of some prepared N-pyrrolyl-ketones provided 1,3-subsituted N-pyrrolyl-alcohols with high diastereoselectivity. Additionally, a deprotection procedure involving an ozonolysis allowed the conversion of the pyrrole-ring into a formamide without loss of optical purity.

METHOD FOR PRODUCING OPTICALLY ACTIVE CARBOXYLIC ACID ESTER

Provided is a method for producing an optically active carboxylic acid ester at a high yield and with high enantioselectivity using dynamic kinetic resolution, said optically active carboxylic acid ester having an α-nitrogen substituent. This method for producing an optically active carboxylic acid ester includes a step in which racemic carboxylic acid represented by formula (a) and a specific alcohol or phenol derivative are reacted in a polar solvent having a dipole moment of at least 3.5 in the presence of an acid anhydride and an asymmetric catalyst, one enantiomer of the racemic carboxylic acid is selectively esterified, and the other enantiomer is racemized. In formula (a), Ra1 represents a nitrogen-containing heteroaromatic ring group bonded to an assymetric carbon via a nitrogen atom constituting a ring, and Ra2 is an organic group.

Synthesis and Stereoselective Reactions of 2-(Pyrrol-1-yl)alkanals and 2-(pyrrol-1-yl)alkan-1-ones

2-(2,5-Dimethylpyrrol-1-yl)alkanals, 2-(pyrrol-1-yl)alkanals, and 2-(2,5-dimethylpyrrol-1-yl)alkan-1-ones were prepared.The reactions of these compounds with Grignard and hydride reagents proceeded stereoselectively to give the corresponding 2-(pyrrol-1-yl)alcohols, which were converted into 2-aminoalcohols, such as norephedrine and ephedrine, by cleavage of the pyrrole ring.