Acetone → (2R)-1-[4-[3-[4-(Cyclopropylcarbonyl)phenoxy]propyl]-1-piperazinyl]-2-[(1-methylethyl)amino]-1-propanone

HRID 411255Notes

Reaction equation

HRID 411255 reaction equation
C([BH3-])#N.[Na+].[NH2:5][C@H:6]([CH3:30])[C:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH:27]3[CH2:29][CH2:28]3)=[O:26])=[CH:21][CH:20]=2)[CH2:11][CH2:10]1)=[O:8].[CH3:31][C:32]([CH3:34])=O>>[CH:27]1([C:25]([C:22]2[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH2:16][CH2:15][N:12]3[CH2:11][CH2:10][N:9]([C:7](=[O:8])[C@H:6]([NH:5][CH:32]([CH3:34])[CH3:31])[CH3:30])[CH2:14][CH2:13]3)=[CH:24][CH:23]=2)=[O:26])[CH2:29][CH2:28]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 9906860A 304121

Product 1

HCID 44304056(2R)-1-[4-[3-[4-(Cyclopropylcarbonyl)phenoxy]propyl]-1-piperazinyl]-2-[(1-methylethyl)amino]-1-propanoneYield 25%

Procedure

Sodium cyanoborohydride (75 mg, 1.2 mmol) was added to a room temperature solution of Example 138 (401 mg, 1 mmol) in acetone (10 mL). After stirring overnight, the reaction mixture was concentrated, and the concentrate was taken up in dichloromethane and washed with water, and brine, dried (Na2SO4), filtered, concentrated and purified by silica gel column chromatography using dichloromethane:methanol (9:1) as the eluant. The product was obtained in 25% yield.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. washwashed with water, and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography
  7. customThe product was obtained in 25% yield

Sources & evidence

ORD record
ord-d6ad7b7576454d32909299eead388320
Source dataset
uspto-grants-2003_05
Patent number
US06559140B2

Reaction notes

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