Piperidine → HCID 67316924, compound

HRID 503619Notes

Reaction equation

HRID 503619 reaction equation
C1C2C(COC([CH2:18][C:19]([N:21]3[CH2:25][C@H:24]([F:26])[CH2:23][C@@H:22]3[C:27]([O:29]C)=O)=[O:20])=O)C3C(=CC=CC=3)C=2C=CC=1.[NH:31]1CCCCC1>CO>[F:26][C@H:24]1[CH2:25][N:21]2[C:19](=[O:20])[CH2:18][NH:31][C:27](=[O:29])[CH:22]2[CH2:23]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 67317845HCID 67317845, compound

Product 1

HCID 67316924HCID 67316924, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A scintillation vial was charged with (2S,4R), (2R,4R)-methyl 1-(2-(((9H-fluoren-9-yl)methoxy)carbonyl)acetyl)-4-fluoropyrrolidine-2-carboxylate (815 mg, 1911 μmol), 19 mL MeOH and piperidine (946 μl, 9556 μmol). The mixture was stirred at RT overnight The mixture was concentrated, dissolved in DCM/MeOH and purified by silica gel chromatography, 50-100% 90/10/1 DCM/MeOH/NH4OH in DCM. (7R)-7-fluoro-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione was isolated as a white solid, and confirmed by 1H-NMR.

Workup

  1. concentrationwas concentrated
  2. dissolutiondissolved in DCM/MeOH
  3. custompurified by silica gel chromatography, 50-100% 90/10/1 DCM/MeOH/NH4OH in DCM

Sources & evidence

ORD record
ord-6357a781aa6d45bf8bddc0384d4146c3
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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