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

HRID 1042888Notes

Reaction equation

HRID 1042888 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-04a9f3dc4f544586af9673bac189ad9e
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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