Ethanol → 4-Amino-3-(benzylthio)-3-methylbutan-1-ol

HRID 504632Notes

Reaction equation

HRID 504632 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([S:14][C:15]([CH3:23])([CH2:19][N+:20]([O-])=O)[CH2:16][CH2:17][OH:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(O)C.O>O1CCCC1>[NH2:20][CH2:19][C:15]([S:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:23])[CH2:16][CH2:17][OH:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 574759763-(Benzylthio)-3-methyl-4-nitrobutan-1-ol

Product 1

HCID 574759774-Amino-3-(benzylthio)-3-methylbutan-1-olYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of lithium aluminum hydride (1.67 g) and tetrahydrofuran (30 ml) was added a solution of 3-(benzylthio)-3-methyl-4-nitrobutan-1-ol (3.00 g) in tetrahydrofuran (10 ml) over 1 hr at room temperature. The reaction mixture was stirred at room temperature for 1 hr, ethanol (10 ml) and water (6.4 ml) were added in this order, and the resulting inorganic salt was removed by filtration. The filtrate was concentrated, and the residue was dissolved in ethyl acetate, dried (MgSO4), and concentrated to give the title compound (2.62 g, yield 99%) as a yellow oil.

Workup

  1. customthe resulting inorganic salt was removed by filtration
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3cd60dcd841341fd812b8d2572c021be
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

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