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

HRID 453580Notes

Reaction equation

HRID 453580 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 warmed to room temperature, and stirred at room temperature for 1 hr. Water and 2N aqueous sodium hydroxide solution were added to the reaction mixture, and the mixture was diluted with ethyl acetate. The mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by NH 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 filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=30:70-100:0)

Sources & evidence

ORD record
ord-51ac9be7da494360bf98e69d1c6e74c6
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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