Journal of Organic Chemistry p. 4535 - 4543 (1989)
Update date:2022-08-04
Topics:
Thomas, Edward W.
Rynbrandt, Ronald H.
Zimmermann, David C.
Bell, Larry T.
Muchmore, Christine R.
Yankee, Ernest W.
The reduction of pyrrolizidinediones 4a and 4b with (i-Bu)2AlH and LiBHEt3 affords the corresponding hexahydro-5-hydroxy-3H-pyrrolizin-3-ones 8a and 8b in good yield.LiBHEt3 also reduces N-methylglutarimide (18) in 53percent yield.The combination of NaBH4/MeOH/Ac2O/CH2Cl2 selectivity reduces an imide in the presence of an ester.Hexahydro-5-(methylthio)-3H-pyrrolizin-3-ones are products of the NaBH4 reduction of pyrrolizidinediones in MeSH/CH2Cl2/Ac2O.The reduction products, thioethers (5a-c) and lactamols (8a-c), are intermediates in the synthesis of pyrrolizinones 1a-c.
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