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

HRID 14273Notes

Reaction equation

HRID 14273 reaction equation
[CH:1]([C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH2:2]>C(O)C.[OH-].[Pd+2].[OH-]>[CH2:1]([C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH3:2]

Participants

4

Reactant 1

HCID 12185972tert-Butyl (2R)-2-ethenylpyrrolidine-1-carboxylate

Product 1

HCID 57487401(S)-N-tert-Butoxycarbonyl-2-ethylpyrrolidineYield 75.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent2×

Procedure

To a suspension of palladium (II) hydroxide on activated carbon (20% by wt, 1.2 g) in 10 mL of ethanol was added tert-butyl (2R)-2-vinylpyrrolidine-1-carboxylate (2.0 g, 10 mmol)as a solution in 15 mL of ethanol and the mixture was placed under 12 psi of H2 on a parr hydrogenator overnight. The resultant mixture was then filtered and concentrated to give tert-butyl (2S)-2-ethylpyrrolidine-1-carboxylate (1.5 g).

Workup

  1. customwas placed under 12 psi of H2 on a parr hydrogenator overnight
  2. filtrationThe resultant mixture was then filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6bfdd633e07b4500adf0ca6da9ac0d78
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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