Methanol → 1,5-Dihydro-4-methyl-3-[[(1R)-1-phenylethyl]amino]-1-(phenylmethoxy)-2H-pyrrol-2-one

HRID 1650778Notes

Reaction equation

HRID 1650778 reaction equation
[CH2:1]([O:8][N:9]1[CH2:13][CH:12]([CH3:14])[C:11](=O)[C:10]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:26]O>>[CH2:1]([O:8][N:9]1[CH2:13][C:12]([CH3:14])=[C:11]([NH:18][C@@H:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:26])[C:10]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 7669N-MethylbenzylamineHCID 14804749HCID 14804749, compound

Product 1

HCID 186393151,5-Dihydro-4-methyl-3-[[(1R)-1-phenylethyl]amino]-1-(phenylmethoxy)-2H-pyrrol-2-oneYield 78%

Procedure

1-Benzyloxy-4-methylpyrrolidin-2,3-dione (7.8 g, 35.6 mmol) and R-(+)-.varies.-methylbenzylamine (8 ml, 7.5 g, 62 mmol) were stirred in methanol (250 ml) at 55° C. for 14 h then refluxed for 4 h. The mixture was then cooled, evaporated and purified by flash chromatography, eluting with hexanes: ethyl acetate (4:1 v/v) to give (R)-1-benzyloxy-4-methyl-2-oxo-3-(1-phenylethylamino)-2,5-dihydropyrrole (8.95 g, 78%) as a slightly yellow oil. 1H NMR (360 MHz, CDCl3) δ7.2-7.5 (10 H, m, Ph's), 5.00 (2 H, s, OCH2), 4.64 (1 H, q, J=6.8 Hz, NCH), 4.1 (1 H, br s, NH), 3.50 (1H, d, J=16.2 Hz, NCHAHB), 3.43 (1 H, d, J=16.2 Hz, NCHAHB), 1.60 (3 H, s, CH3CCH2), 1.45 (3 H, d, J=6.8 Hz, CH3CHPh), m/z (CI, NH3) 323 (M+ +H).

Workup

  1. temperaturethen refluxed for 4 h
  2. temperatureThe mixture was then cooled
  3. customevaporated
  4. custompurified by flash chromatography
  5. washeluting with hexanes: ethyl acetate (4:1 v/v)

Sources & evidence

ORD record
ord-edda2503ad2a4846aa98e88f765a1edf
Source dataset
uspto-grants-1990_05
Patent number
US04925867

Reaction notes

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