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

HRID 2245430Notes

Reaction equation

HRID 2245430 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:13][CH2:12][C@H:11]([OH:14])[C@H:6]1[C:7](OC)=[O:8])=[O:4].[NH3:15]>CO>[OH:14][C@@H:11]1[CH:6]2[C:7](=[O:8])[NH:15][CH2:2][C:3](=[O:4])[N:5]2[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59215866methyl (3S)-1-(chloroacetyl)-3-hydroxy-L-prolinate

Product 1

HCID 59215828(8S)-8-hydroxyhexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto afford a solid

Sources & evidence

ORD record
ord-4c1e3f8623fc4294829c7bcae6a03d0b
Source dataset
uspto-grants-2010_03
Patent number
US07683056B2

Reaction notes

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