Water → 2-(Benzylthio)-3,3-dimethoxypropan-1-amine

HRID 504642Notes

Reaction equation

HRID 504642 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][CH:9]([O:23][CH3:24])[CH:10]([S:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:11][N+:12]([O-])=O.O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:16]([S:15][CH:10]([CH:9]([O:8][CH3:7])[O:23][CH3:24])[CH2:11][NH2:12])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59135946({[2,2-Dimethoxy-1-(nitromethyl)ethyl]thio}methyl)benzene

Product 1

HCID 574759902-(Benzylthio)-3,3-dimethoxypropan-1-amineYield 76.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of lithium aluminum hydride (13.0 g) in tetrahydrofuran (60 ml) was added dropwise a solution (76 ml) of ({[2,2-dimethoxy-1-(nitromethyl)ethyl]thio}methyl)benzene (18.6 g) in tetrahydrofuran at 0° C. The reaction mixture was allowed to warm to room temperature, and stirred at room temperature for 1 hr. Water and 2N aqueous sodium hydroxide solution were added to the reaction solution, and the mixture was diluted with ethyl acetate. The mixture was filtrated through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=30:70-100:0) to give the title compound (12.6 g, yield 76%) as a yellow oil.

Workup

  1. filtrationThe mixture was filtrated through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=30:70-100:0)

Sources & evidence

ORD record
ord-11bbbfae65904c25bf14d525a3d40e80
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

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