Tetrahydro-4H-pyran-4-one → HCID 58718610, compound

HRID 1244857Notes

Reaction equation

HRID 1244857 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[O:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.[H][H]>C(O)C.[Pd]>[O:14]1[CH2:19][CH2:18][CH:17]([NH:1][C@H:2]2[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]2)[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 58718610HCID 58718610, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate was added to a solution of tetrahydro-4H-pyran-4-one and 10% Pd/C (300 mg) in ethanol and the reaction mixture left under about 415 kPa (about 60 psi) of hydrogen gas for 18 hours. The reaction mixture was filtered through Arbocel®, washing through thoroughly with ethyl acetate. The filtrate was concentrated in vacuo and the crude product purified by column chromatography on silica gel to yield the desired product, 6.7 g (61%).

Workup

  1. filtrationThe reaction mixture was filtered through Arbocel®
  2. washwashing through thoroughly with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe crude product purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ef92a52b180645b2b47b0dca895bca2a
Source dataset
uspto-grants-2006_10
Patent number
US07122683B2

Reaction notes

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