HCID 57803338, compound → HCID 60054959, compound

HRID 2103385Notes

Reaction equation

HRID 2103385 reaction equation
[CH2:1]([O:8][C@H:9]1[CH2:13][N:12](C(OCC2C=CC=CC=2)=O)[C@H:11]([C:24]([CH3:26])=[CH2:25])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Pd]>[CH2:1]([O:8][C@H:9]1[CH2:13][NH:12][C@H:11]([CH:24]([CH3:26])[CH3:25])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 57803338HCID 57803338, compound

Product 1

HCID 60054959HCID 60054959, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl (2S,4R)-4-(benzyloxy)-2-isopropenylpyrrolidine-1-carboxylate (1.00 g, 2.84 mmol) was dissolved in ethanol (40 mL) and then 5% Pd—C (100 mg) was added to the solution. The flask was purged with hydrogen and then shaken on a Parr under 53 psi atmosphere of hydrogen for 17 hours. The reaction was then flushed with nitrogen and filtered through Celite on a glass frit and washed with methanol. The filtrate was concentrated and chromatographed on silica gel (1% triethylamine/10% methanol/89% ethyl acetate) to furnish the amine as a pale yellow oil, 0.53 g (85%).

Workup

  1. customThe flask was purged with hydrogen
  2. customThe reaction was then flushed with nitrogen
  3. filtrationfiltered through Celite on a glass frit
  4. washwashed with methanol
  5. concentrationThe filtrate was concentrated
  6. customchromatographed on silica gel (1% triethylamine/10% methanol/89% ethyl acetate)

Sources & evidence

ORD record
ord-9b1a4a9414a549ac8226c026bbee5cec
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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