Water → (s)-n-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-n-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine

HRID 429838Notes

Reaction equation

HRID 429838 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([N:13]([C:16]([CH:18]3[CH2:23][CH2:22][N:21]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:20][CH2:19]3)=O)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([N:13]([CH2:16][CH:18]3[CH2:23][CH2:22][N:21]([S:24]([CH3:27])(=[O:25])=[O:26])[CH2:20][CH2:19]3)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20706300(s)-n-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-n-ethyl-(1-methanesulfonylpiperidin-4-ylcarbonyl)amineHCID 21226445Aluminium lithium hydride

Product 1

HCID 10927016(s)-n-[2-(2,3,-Dihydrobenzofuran-5-yl)-1-methylethyl]-n-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amineYield 53.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-methanesulfonylpiperidin-4-ylcarbonyl)amine (2.21 g, 5 mmol) in tetrahydrofuran (5 ml) was added dropwise to a suspension of lithium aluminum hydride (0.38 g, 10 mmol) in tetrahydrofuran (10 ml) at 0° C., under a nitrogen atmosphere. The mixture was heated at reflux temperature for 2 hours and cooled to room temperature. Water (380 ml) was added dropwise to the mixture, followed by 15% sodium hydroxide (380 ml), and additional water (1550 μL). The mixture was stirred at room temperature for about 15 minutes and filtered. The filtrate was washed and rinsed with dichloromethane. Evaporation of the solvent gave a colorless oil, which solidified upon standing. Recrystallization from ethyl acetate/hexane (1:1) gave (S)-N-[2-(2,3,-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-methanesulfonylpiperidin-4-ylmethyl)amine as colorless crystals (1.02 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 2 hours
  3. filtrationfiltered
  4. washThe filtrate was washed
  5. washrinsed with dichloromethane
  6. customEvaporation of the solvent
  7. customgave a colorless oil, which
  8. customRecrystallization from ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-1c6b35627c4642d5a2a3700c20fb5df8
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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