(1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine hydrochloride Chemical Properties

Melting point:

>172°C (dec.)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

White

InChI

InChI=1/C9H9F2N.ClH/c10-7-2-1-5(3-8(7)11)6-4-9(6)12;/h1-3,6,9H,4,12H2;1H/t6-,9+;/s3

InChIKey

IMYLOCHFFLYHPS-RHUSADAZNA-N

SMILES

N[C@@H]1C[C@H]1C1C=CC(F)=C(F)C=1.Cl |&1:1,3,r|

(1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine hydrochloride Usage And Synthesis

Uses

(1S,2R)-2-(3,4-Difluorophenyl)-cyclopropanamine is an intermediate used to prepare ticagrelor (T437700).

Synthesis Reference(s)

Synthesis of 2-(3,4-difluorophenyl)cyclopropanamine derivatives and salts. EU Patent EP2644590A1

Synthesis

1,2-Difluorobenzene is reacted with 3-chloropropionyl chloride to produce 3-chloro-1-(3',4'-difluorophenyl)-propan-1-one, which is by addition of N,N-dimethylformamide, phloroglucinol and sodium iodide in the next step converted to 1-(3',4'-difluorophenyl)-3-nitro-propan-1-one. The keto group of the latter intermediate is in the subsequent step stereochemically reduced to hydroxyl group by the use of chiral oxazaborolidine together with borane dimethyl sulfide or borane-N,N-diethyl aniline complex in the presence of tetrahydrofurane. The obtained (1R)-1-(3',4'-difluorophenyl)-3-nitro-propan-1-ol is then added to a mixture of triphenylphosphine and diethylazodicarboxylate in benzene to yield (1S,2R)-2-(3',4'-difluorophenyl)-1-nitrocyclopropane, which is in the last step converted to 2-(3,4-difluorophenyl)cyclopropane amine by reduction of the nitro group by catalytic hydrogenation with palladium catalyst and zink dust. 

(1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine hydrochloride(1156491-10-9)Related Product Information

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