tert-Butyl (2R)-2-ethenylpyrrolidine-1-carboxylate → (S)-N-tert-Butoxycarbonyl-2-ethylpyrrolidine

HRID 2261898Notes

Reaction equation

HRID 2261898 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH:13]=[CH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[CH2:13]([C@H:9]1[CH2:10][CH2:11][CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH3:14]

Participants

5

Reactant 2

HCID 12185972tert-Butyl (2R)-2-ethenylpyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 57487401(S)-N-tert-Butoxycarbonyl-2-ethylpyrrolidineYield 84.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Tert-butyl-(2R)-2-vinylpyrrolidine-1-carboxylate (0.21 g, 1.07 mmol) was dissolved in methanol (10 mL) with palladium on carbon, 10% catalyst (0.046 g, 20% by wt.) and subjected to a hydrogen atmosphere via balloon. The reaction was run overnight and filtered through Celite and concentrated in vacuo to yield tert-butyl (2S)-2-ethylpyrrolidine-1-carboxylate (0.18 g, HPLC RT=3.00 min.). LC-MS m/z (minus t-butyl+CH3CN+1)=185. 1H NMR (CD3OD, 400 Mhz) 3.67-3.63 ppm (m, 1H), 3.36-3.30 (m, 2H), 1.92-1.71 (m, 4H), 1.45 (s, 9H), 1.43-1.29 (m, 2H), 0.90-0.85 (t, 3H).

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5a5b6fe274c46e794a8176f224709ae
Source dataset
uspto-grants-2010_12
Patent number
US07847100B2

Reaction notes

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