D-Psicose → 2-(2-Morpholin-4-yl-2-oxo-ethyl)-2-(3-phenyl-propyl)-malonic acid diethyl ester

HRID 1830142Notes

Reaction equation

HRID 1830142 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[C:5]([CH2:20][C:21]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:22])([CH2:11][CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>CCO.[Pd]>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:20][C:21]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:22])([CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:29])[CH3:10]

Participants

5

Reactant 2

HCID 441036D-PsicoseHCID 694346602-(2-Morpholin-4-yl-2-oxo-ethyl)-2-(3-phenyl-allyl)-malonic acid diethyl ester

Product 1

HCID 210257122-(2-Morpholin-4-yl-2-oxo-ethyl)-2-(3-phenyl-propyl)-malonic acid diethyl esterYield 100.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(2-morpholin-4-yl-2-oxo-ethyl)-2-(3-phenyl-allyl)-malonic acid diethyl ester (257 mg, 0.637 mmol) in EtOH (15 ml) was hydrogenated over Pd/C at 55 Psi for 7.5 hrs. The catalyst filtered off over a pad of Celite and the filtrate evaporated under vacuum to give 2-(2-morpholin-4-yl-2-oxo-ethyl)-2-(3-phenyl-propyl)-malonic acid diethyl ester as a light yellow oil (260 mg); 1H NMR (CDCl3) 7.4–7.1 (m, 5H), 4.20 (q, J=7.1 Hz, 4H), 3.7–3.4 (m, 8H), 3.0 (s, 2H), 2.6 (t, J=7.6 Hz, 2H), 2.2 (m, 2H), 2.55 (m, 2H), 1.20 (t, J=7.1 Hz, 6H). MS: 406 (MH+).

Workup

  1. filtrationThe catalyst filtered off over a pad of Celite
  2. customthe filtrate evaporated under vacuum

Sources & evidence

ORD record
ord-72492e15794e48e59388640640987348
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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