Butanal → HCID 68779815, compound

HRID 1876814Notes

Reaction equation

HRID 1876814 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH3:4].[BH3-]C#N.[Na+].[Cl:10][C:11]1[CH:12]=[C:13]([CH2:18][C:19]([N:21]2[CH:30]3[CH:25]([CH2:26][CH2:27][CH2:28][CH:29]3[N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[NH:24][CH2:23][CH2:22]2)=[O:20])[CH:14]=[CH:15][C:16]=1[Cl:17].C([O-])([O-])=O.[Na+].[Na+]>CO.C(O)(=O)C>[CH2:1]([N:24]1[CH:25]2[CH:30]([CH:29]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:28][CH2:27][CH2:26]2)[N:21]([C:19](=[O:20])[CH2:18][C:13]2[CH:14]=[CH:15][C:16]([Cl:17])=[C:11]([Cl:10])[CH:12]=2)[CH2:22][CH2:23]1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 261ButanalHCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 687760732-(3,4-dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one

Product 1

HCID 68779815HCID 68779815, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

Butyraldehyde (93 mg, 1.3 mmol) was dissolved in 5 ml of MeOH and NaBH3CN (82 mg, 1.3 mmol) was added. The pH was adjusted to 5 with concentrated acetic acid. 2-(3,4-Dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one (101 mg, 0.25 mmol), dissolved in MeOH (15 ml), was then added to the mixture and the mixture was stirred at room temperature overnight. After addition of saturated Na2CO3 solution (15 ml), the mixture was stirred at room temperature for 15 minutes. The precipitate formed was filtered off. The aqueous phase of the filtrate was extracted three times with CH2Cl2 and the combined organic phases were dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash chromatography (Ø 2 cm, CH2Cl2/MeOH/NH3 9.5:0.5:0.1, l=15 cm, V=5 ml). A colorless resin was isolated.

Workup

  1. additionwas then added to the mixture
  2. stirringthe mixture was stirred at room temperature for 15 minutes
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. extractionThe aqueous phase of the filtrate was extracted three times with CH2Cl2
  6. dry with materialthe combined organic phases were dried over Na2SO4
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography (Ø 2 cm, CH2Cl2/MeOH/NH3 9.5:0.5:0.1, l=15 cm, V=5 ml)
  9. customA colorless resin was isolated

Sources & evidence

ORD record
ord-6a54bc8aa9514737818cc1ff8f621dc7
Source dataset
uspto-grants-2012_11
Patent number
US08309725B2

Reaction notes

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