HCID 11000775, compound → HCID 11106374, compound

HRID 1656146Notes

Reaction equation

HRID 1656146 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][N:12](CC2C=CC=CC=2)[C@@H:11]([CH3:21])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][NH:12][C@@H:11]([CH3:21])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11000775HCID 11000775, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11106374HCID 11106374, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 4.500 g (15.50 mmol) sample of (2S,4S)-4-t-butoxycarbonylamino-2-methyl-1-N-benzylpyrrolidine, from Example 2 above, was dissolved in 150 mL of methanol, 0.90 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 3.081 g of the title compound as a white solid. MS M/Z: 201 (M+H). NMR (CDCl3) δ: 1.15 (d, 3H, J=6 Hz), 1.44 (s, (1H), 1.54-1.63 (m, 2H), 1.75 (m, 1H), 2.64 (dd, 1H, J=5, J=12 Hz), 3.26 (m, 1H), 3.38 (dd, 1H, J=7, J=12 Hz), 4.12 (br, 1H), 4.63 (br, 1H). IR (KBr): 1685 cm-1.

Workup

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

Sources & evidence

ORD record
ord-08af5d17cefd4e17be5a5f426d9fb6d6
Source dataset
uspto-grants-1993_10
Patent number
US05252747

Reaction notes

Loading…