199395-81-8

Basic information

• Product Name: Butanamide, N-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-
• Synonyms: Butanamide, N-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-
• CAS NO: 199395-81-8
• Molecular Formula: C10H17NO2
• Molecular Weight: 183.25
• Mol File: 199395-81-8.mol

Chemical Properties

• Boiling Point: 379.0±31.0 °C(Predicted)
• Appearance: /
• Density: 1.06±0.1 g/cm3(Predicted)
• PKA: 14.86±0.10(Predicted)
• CAS DataBase Reference: Butanamide, N-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanamide, N-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-(199395-81-8)
• EPA Substance Registry System: Butanamide, N-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-(199395-81-8)

Safety Data

• Hazardous Substances Data: 199395-81-8(Hazardous Substances Data)

Upstream product

• 168960-19-8 (1S,4R)-1-amino-4-hydroxymethyl-2-cyclopentene hydrochloride 
• 584-08-7 potassium carbonate 
• 141-75-3 butyryl chloride 
• 168960-19-8 (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride 

Relevant articles and documents

Process for the preparation of aminoalcohol derivatives and their further conversion to (1R, 4S)-4-((2-amino-6-chloro-5-formamido-4-pyrimidinyl)-amino)-2-cyclopentenyl-1- methanol

The invention relates to a novel process for the preparation of an aminoalcohol of the formula 1racemically or optically active, starting from 2-azabi-cyclo[2.2.1]hept-5-en-3-one, its further conversion to give the corresponding acyl derivative and its further conversion to (1S,4R)- or (1R,4S)-4-(2-amino-6-chloro-9-H-purine-9-yl)-2-cyclopentenyl-1-methanol of the formulae 2In the latter synthesis, the aminoalcohol is converted into the corresponding D- or L-tartrate, which is then reacted with N-(2-amino-4,6-dichloropyrimidin-5-yl) formamide of the formula 3to give (1S,4R)- or (1R,4S)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopentenyl-1-methanol of the formulae 4and then cyclized to give the end compounds.

Enantiomer compositions of (1R,4S)-1-butyrylamino-4-(hydroxymethyl)-2-cyclopentene

A novel process for the preparation of (1S,4R)- or (1R,4S)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol of the formulae is described. This entails in the first stage (+/-)-2-azabicyclo[2.2.1]hept-5-en-3-one of the formula being acylated to give a (+/-)-2-azabicyclo[2.2.1]hept-5-en-3-one derivative of the general formula in which R1 denotes C1-4-alkyl, C1-4-alkoxy, aryl or aryloxy, the latter being reduced in the second stage to give a cyclopentene derivative of the general formula in which R1 has the stated meaning, the latter then being converted in the third stage biotechnologically into the (1R,4S)- or (1S,4R)-1-amino-4-(hydroxymethyl)-2-cyclopentene of the formula the latter being converted in the fourth stage with N-(2-amino-4,6-dichloro-5-pyrimidinyl)formamide of the formula into the (1S,4R)- or (1R,4S)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol of the formulae and the latter being cyclized in the fifth stage in a known manner to the final product of the formula I or II.