Piperidine → (S)-7,7-difluoro-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

HRID 1013747Notes

Reaction equation

HRID 1013747 reaction equation
C1C2C(COC([CH2:18][C:19]([N:21]3[CH2:25][C:24]([F:27])([F:26])[CH2:23][C@@H:22]3[C:28]([O:30]C)=O)=[O:20])=O)C3C(=CC=CC=3)C=2C=CC=1.[NH:32]1CCCCC1>CO>[F:26][C:24]1([F:27])[CH2:25][N:21]2[C:19](=[O:20])[CH2:18][NH:32][C:28](=[O:30])[C@@H:22]2[CH2:23]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 67318151(R)-methyl 1-(2-(((9H-fluoren-9-yl)methoxy)carbonyl)acetyl)-4,4-difluoropyrrolidine-2-carboxylate

Product 1

HCID 67316882(S)-7,7-difluoro-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A round bottom flask was charged with (R)-methyl 1-(2-(((9H-fluoren-9-yl)methoxy)carbonyl)acetyl)-4,4-difluoropyrrolidine-2-carboxylate (1.10 g, 2475 μmol) and 25 mL MeOH. Piperidine (1225 μl, 12375 μmol) was added, and the mixture was stirred at RT overnight. The mixture was concentrated and purified by silica gel chromatography, DCM in 90/10 DCM/MeOH to provide (S)-7,7-difluoro-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione as a white solid. GC/MS: [M+H]=191.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel chromatography, DCM in 90/10 DCM/MeOH

Sources & evidence

ORD record
ord-19bf34c44876413a81200c9819c42763
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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