HCID 57718920, compound → HCID 57719093, compound

HRID 1985242Notes

Reaction equation

HRID 1985242 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH:12]2[N:16]([CH2:17][CH2:18][CH3:19])[C:15](=[O:20])[N:14]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[C:13]2=O)=[CH:5][CH:4]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][CH:12]2[CH2:13][N:14]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)[C:15](=[O:20])[N:16]2[CH2:17][CH2:18][CH3:19])=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 57718920HCID 57718920, compound

Product 1

HCID 57719093HCID 57719093, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-[3-(4-methoxy-phenyl)-propyl]-3-(4-methyl-benzyl)-1-propyl-imidazolidine-2,4-dione (1.26 g, 3.19 mmol) in THF (20 ml) was treated dropwise with 1 M solution of borane-THF complex in THF (16 mL, 16 mmol) and then stirred at room temperature under N2 for 22 h. The reaction was quenched with methanol (20 mL) and stirred at room temperature for 2 hr. The solvent was removed in vacuo to give 1.25 g (100%) crude 4-[3-(4-methoxy-phenyl)-propyl]-1-(4-methyl-benzyl)-3-propyl-imidazolidin-2-one that was carried on without purification. MS (ES+) Calc'd for C24H33N2O2 (M+1) 381. Found m/z 381 (100%). 1H NMR.

Workup

  1. customThe reaction was quenched with methanol (20 mL)
  2. stirringstirred at room temperature for 2 hr
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4ab46e932d1b4a1fa52663b9996e7ee7
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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