Dimethyl Sulfoxide → HCID 83670762, compound

HRID 240430Notes

Reaction equation

HRID 240430 reaction equation
[O:1]=[C:2]1[CH:6]2[CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][N:5]2[CH2:4][CH:3]1C(OC)=O.CS(C)=O.[Na+].[Cl-]>O>[O:1]=[C:2]1[CH:6]2[CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][N:5]2[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 86680441HCID 86680441, compound

Product 1

HCID 83670762HCID 83670762, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
130 °C

Procedure

A mixture of 2-tert-butyl 7-methyl 8-oxohexahydropyrrolo[1,2-a]pyrazine-2,7(1H)-dicarboxylate (Example 35B, 131 g, 0.44 mol), dimethyl sulfoxide (530 mL), NaCl (25.6 g, 0.44 mol) and water (32 g, 1.75 mol) was heated to 130° C. and maintained at that temperature for 2 hours. The reaction mixture was cooled, diluted with water (1 L) and extracted with ethyl acetate (1 L×2). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was chromatographed over silica gel eluting with 30-40% ethyl acetate in petroleum ether to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.48 (s, 9H), 2.23-2.42 (m, 3H), 2.47-2.60 (m, 1H), 2.60-2.78 (m, 1H), 2.82-2.98 (m, 1H), 3.02-3.10 (m, 1H), 3.32-3.40 (m, 1H), 3.65-3.85 (m, 1H), 3.99-4.20 (bs, 1H), 4.20-4.45 (bs, 1H).

Workup

  1. temperaturemaintained at that temperature for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ethyl acetate (1 L×2)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed over silica gel eluting with 30-40% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-417b36be905b4dc3bb0ac99457dc9d10
Source dataset
uspto-grants-2014_02
Patent number
US08648074B2

Reaction notes

Loading…