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Synthesis of (R, S)-[2,3-13C2]-1-(1′-methyl-2′-pyrrolidinyl)propan-2-one; {(R, S)-[2′,3′-13C2]hygrine}

✍ Scribed by Timothy W. Abraham; Edward Leete

Publisher
John Wiley and Sons
Year
1996
Tongue
French
Weight
317 KB
Volume
38
Category
Article
ISSN
0022-2135

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✦ Synopsis

2-Ethoxy-1-methyl-5-pymlidinone (1) was reacted with ethyl [3,4-'3C2]acetoacetate (2) in the presence of T i c 4 to give ethyl [3,4-13C2]-2-( 1'-methyl-5'oxo-2'-pyrrolidinyl)-3-oxobutanoate (3) in 85% yield. Decarboethoxylation of ethyl [3,4-13C2]-2-( l'-methyl-5'-oxo-2'-pyrrolidiny1)-3-oxobutanoate (3) was accomplished using NaCl and HzO in DMSO to give (R,S)-[2,3-13C~]-l-(l'-methyl-5'oxo-2'-p~olidinyl)propan-2-one (4) in 91% yield. Protection of the ketone as a ketal (ethylene glycol, H+), followed by reduction of the amide to the amine using LiAlH4 and subsequent deprotection of the ketal gave (R,S)-[2,3-13C2]-I-( 1'methyl-2'-pyrrolidinyl)propan-2-one ((R,S)-[2',3'-13C2]Hygrine) (8) in 78% yield. (61 % overall yield from ethyl [3,4-13C~]acetoacetate).

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