Hydrochloric Acid → 4-(R)-(2-Furyl)carbonyl-1-[1-(R)-phenylethyl]-2-pyrrolidone

HRID 1883963Notes

Reaction equation

HRID 1883963 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[Mg]Br.O1C=CC=C1.CN(OC)[C:15]([CH:17]1[CH2:21][C:20](=[O:22])[N:19]([C@@H:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH3:24])[CH2:18]1)=[O:16].Cl>O1CCCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:15]([C@H:17]1[CH2:18][N:19]([C@@H:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH3:24])[C:20](=[O:22])[CH2:21]1)=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8029FuranHCID 18439411N-methyl-N-methoxy-1-[1-(R)-phenylethyl]-5-oxopyrrolidine-3-carboxamideHCID 178419635HCID 178419635, compound

Product 1

HCID 184394054-(R)-(2-Furyl)carbonyl-1-[1-(R)-phenylethyl]-2-pyrrolidoneYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an atmosphere of nitrogen, 0.5 mol/1 of 2-furylmagnesium bromide (180 ml) prepared from furan was added dropwise to a tetrahydrofuran solution (160 ml) of N-methyl-N-methoxy-1-[1-(R)-phenylethyl]-5-oxopyrrolidine-3-carboxamide (8.30 g, 30.0 mmol), and the mixture was stirred for 30 minutes. The reaction solution was mixed with 1 mol/1 hydrochloric acid (200 ml) under ice-cooling and extracted with ethyl acetate (200 ml×2), and then the organic layer was washed with saturated brine (100 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure and the resulting residue was applied to a silica gel column chromatography. By eluting with a n-hexane:ethyl acetate system of from (1:1) to (1:2), 3.94 g (46%) of the title compound was obtained as a light yellow oil. 1H-NMR (400 MHz, CDCl3) δ: 1.55 (3 H, d, J=6.84 Hz), 2.72-2.87 (2 H, m), 3.20-3.25 (1 H, m), 3.67 (1 H, dd, J=6.83, 9.77 Hz), 3.80-3.89 (1 H, m), 5.53 (1 H, q, J=6.84 Hz), 6.57 (1 H, dd, J=1.46, 3.42 Hz), 7.18-7.38 (6 H, m), 7.60 (1 H, d, J=0.98 Hz).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate (200 ml×2)
  3. washthe organic layer was washed with saturated brine (100 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under a reduced pressure
  6. washBy eluting with a n-hexane

Sources & evidence

ORD record
ord-9a7acb664f29460da876a1c5b9b2a884
Source dataset
uspto-grants-2004_07
Patent number
US06762181B1

Reaction notes

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