Ethyl ketone → HCID 10662297, compound

HRID 1635556Notes

Reaction equation

HRID 1635556 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[O:17].[CH3:18][CH2:19][C:20](=O)[CH2:21][CH3:22].C(N(CC)CC)C.C([BH3-])#N.[Na+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:11][O:10][C:8]([C:6]1[CH:5]=[CH:4][C:3]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])=[C:2]([NH:1][CH:20]([CH2:21][CH3:22])[CH2:19][CH3:18])[CH:7]=1)=[O:9]

Participants

7

Reactant 4

HCID 7288Ethyl ketoneHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 10585757HCID 10585757, compound

Product 1

HCID 10662297HCID 10662297, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(2-amino-4-methoxycarbonylphenyl)pyrrolidin-2-one (0.5 g, 2.1 mmol) from example 2, 3-pentanone (0.19 g, 2.2 mmol) and triethylamine (0.44 g, 4.3 mmol) in 10 mL of dry dichloromethane was treated with 1 m solution of titanium tetrachloride (3.5 mL, 3.5 mmol) in dichloromethane. The resulting mixture was stirred at ambient temperature for 18 h after which time sodium cyanoborohydride (0.41 g, 6.5 mmol) was added. Stirring was continued for an addition 3 h. The reaction mixture was quenched with 1 N sodium hydroxide (2 mL) and the organic layer was separated and concentrated under vacuum. The residue was extracted with ethyl acetate (3×30 mL) and the combined extracts were dried and concentrated to give an oil which was purified by column chromatography (silica gel; 10% ethanol in ether) to yield 0.16 g (25%) of 1-[4-methoxycarbonyl-2-(3-pentylamino)phenyl]pyrrolidin-2-one.

Workup

  1. additionwas added
  2. additionwas continued for an addition 3 h
  3. customThe reaction mixture was quenched with 1 N sodium hydroxide (2 mL)
  4. customthe organic layer was separated
  5. concentrationconcentrated under vacuum
  6. extractionThe residue was extracted with ethyl acetate (3×30 mL)
  7. customthe combined extracts were dried
  8. concentrationconcentrated
  9. customto give an oil which
  10. customwas purified by column chromatography (silica gel; 10% ethanol in ether)

Sources & evidence

ORD record
ord-b6a25a44e2e448bc88ad2fbdd4d0a3bd
Source dataset
uspto-grants-2003_01
Patent number
US06509359B1

Reaction notes

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