HCID 54352100, compound → HCID 10197748, compound

HRID 1656145Notes

Reaction equation

HRID 1656145 reaction equation
[C:1]([NH:4][C@@H:5]1[CH2:9][N:8](CC2C=CC=CC=2)[C@@H:7]([CH3:17])[CH2:6]1)(=[O:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([NH:4][C@@H:5]1[CH2:9][NH:8][C@@H:7]([CH3:17])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 54352100HCID 54352100, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10197748HCID 10197748, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 2.93 g (12.61 mmol) sample of (2S,4S)-4-acetylamino-2-methyl-1-N-benzylpyrrolidine, from Example 1, step g above, was dissolved in 50 mL of methanol, 0.60 g of 10% Pd/C was added and the mixture shaken under 4 atm of hydrogen at room temperature for 13 hours. The mixture was concentrated, the catalyst was removed by filtration, and the solvent removed to afford 1.688 g (94.1% yield) of the title compound as a white solid. MS M/Z: 143 (M+H). NMR (CDCl3) δ: 1.16 (d, 3H, J=6 Hz), 1.63 (m, 1H), 1.79 (m, 1H), 1.95 (s, 3H), 2.65 (m, 1H), 3.28 (m, 1H), 3.41 (m, 1H), 4.40 (m, 1H), 5.81 (br, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe catalyst was removed by filtration
  3. customthe solvent removed

Sources & evidence

ORD record
ord-b9d6834d100e4f80a9847c02139177a9
Source dataset
uspto-grants-1993_10
Patent number
US05252747

Reaction notes

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