Ammonia → (8S)-8-hydroxyhexahydropyrrolo[1,2-a]pyrazine-1,4-dione

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Reaction Steps

A mixture of methyl (3S)-1-(chloroacetyl)-3-hydroxy-L-prolinate (D69, 1.48 g, 6.7 mmol) in 10 ml of MeOH and 60 ml of a saturated solution of NH3 in MeOH was stirred for 48 h at rt. The solvent was evaporated under reduced pressure, to afford a solid. Analysis indicated this to be the title compound as a pair of diastereoisomers. After a short chromatography column (CHCl3/MeOH 8/2 as eluent) the title compound was isolated as a foamy solid (1 g). Yield 88%. Reference: Khimiko-Farmatsevticheskii Zhurnal 1984, 18, 1445-8

Provenance & Evidence