HCID 23052519, compound → HCID 67791159, compound

HRID 1650782Notes

Reaction equation

HRID 1650782 reaction equation
[CH2:1]([O:8][N:9]1[CH2:13][C:12]([CH2:14][CH3:15])=[C:11]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:10]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.C(O)(=O)C>[CH2:1]([O:8][N:9]1[CH2:13][C@H:12]([CH2:14][CH3:15])[C@H:11]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:10]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 23052519HCID 23052519, compound

Product 1

HCID 67791159HCID 67791159, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Benzyloxy-4-ethyl-3-(4-methoxybenzylamino)-2-oxo-2,5-dihydropyrrole (72 mg, 205 μmol) was hydrogenated on platinum (IV) oxide (9.6 mg) in ethyl acetate (10 ml) and acetic acid (100 μl) at atmospheric pressure for 20 h. The mixture was filtered, washed with sodium hydrogen carbonate solution and brine, dried (MgSO4), and evaporated in bacuo to give cis-1-benzyloxy-4-ethyl-3-(4-methoxybenzylamino)pyrrolidin-2-one (72 mg, 100%) as an oil. 1H NMR (250 MHz, CDCl3) δ7.3-7.5 (5 H, m, Ph), 7.26 (2 H, d, J=9 Hz, MeOCCH), 6.84 (2 H, d, J=9 Hz MeOCCHCH), 4.98 (2 H, s, OCH2), 3.80 (2 H, s, CH2NH), 3.78 (3 H, s, OMe), 3.30 (1 H, d, J=8.5 Hz, NCH), 3.25 (1 H, dd, J=6 and 10 Hz, CHAHBNO), 2.95 (1 H, dd, J=3 and 10 Hz, CHAHBNO), 2.0-2.1 (1 H, m, CHCH2), 1.5-1.6 and 1.0-1.1 (2 H, m, CH2CH3), 0.74 (3 H, t, J=7.5 Hz, CH3), m/z (CI, NH3) 249 (M-MeOC6H4 +H).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with sodium hydrogen carbonate solution and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in bacuo

Sources & evidence

ORD record
ord-e1ea6aba628947c98a0267c1c846085a
Source dataset
uspto-grants-1990_05
Patent number
US04925867

Reaction notes

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