HCID 69735074, compound → HCID 10848154, compound

HRID 1421669Notes

Reaction equation

HRID 1421669 reaction equation
[C:1]1(=[O:25])[N:5]([CH2:6][CH2:7][NH:8][CH2:9][CH2:10][CH:11](CC2C=CC=CC=2)[OH:12])[C:4](=[O:20])[C:3]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:2]12>[Pd].CO.C(O)(=O)C>[C:4]1(=[O:20])[N:5]([CH2:6][CH2:7][NH:8][CH2:9][CH2:10][CH2:11][OH:12])[C:1](=[O:25])[C:2]2=[CH:24][CH:23]=[CH:22][CH:21]=[C:3]12

Participants

4

Reactant 1

HCID 69735074HCID 69735074, compound

Product 1

HCID 10848154HCID 10848154, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

N-Phthalimidoethyl(benzyl)-3-amino-1-propanol (4.62 g, 11.95 mmol), Pd/C 10% (1 g) and MeOH:acetic acid (95:5, v/v) (100 mL) was transferred to a 250 mL par hydrogenation flask. The flask was purged and filled with H2 three times and then left under H2 at 55 psi with shaking. The mixture absorbed 20 psi of H2 in 30 minutes. The shaking was stopped and the pressure was raised to 55 psi again. After 3 hrs the pressure was 45 psi so the pressure was increased to 55 psi once more. The reaction was complete as indicated by TLC dichloromethane:MeOH (9:1, v/v) in 4 hours. The reaction mixture was filtered though a bed of celite and the solvent evaporated under vacuo to leave a yellowish oil. The oil was purified by silica gel flash column chromatography using dichloromethane:MeOH (9:1, v/v) as the eluent. The appropriate fractions were combined and concentrated under vacuo to afford 2.51 g (68%) of the title compound as a white solid (m.p. 94-95° C.).

Workup

  1. customThe flask was purged
  2. additionfilled with H2 three times
  3. waitleft under H2 at 55 psi
  4. customThe mixture absorbed 20 psi of H2 in 30 minutes
  5. temperaturethe pressure was raised to 55 psi again
  6. temperature45 psi so the pressure was increased to 55 psi once more
  7. waitv/v) in 4 hours
  8. filtrationThe reaction mixture was filtered though a bed of celite
  9. customthe solvent evaporated under vacuo
  10. customto leave a yellowish oil
  11. customThe oil was purified by silica gel flash column chromatography
  12. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-a0f7af1c1de94ae3af61c9e8619f32ba
Source dataset
uspto-grants-2000_06
Patent number
US06077954

Reaction notes

Loading…