Sodium Sulfate → (S)-2-Amino-4-(2-chloro-phenyl)-2-methyl-butan-1-ol

HRID 1911552Notes

Reaction equation

HRID 1911552 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C@:10]([NH2:21])([CH3:20])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[NH2:21][C@@:10]([CH3:20])([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])[CH2:9][OH:8]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 68711125(S)-2-Amino-4-(2-chloro-phenyl)-2-methyl-butyric acid methyl ester

Product 1

HCID 68712118(S)-2-Amino-4-(2-chloro-phenyl)-2-methyl-butan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (0.072 g, 1.9 mmol) in tetrahydrofuran (10 ml) was added a solution of (S)-2-amino-4-(2-chloro-phenyl)-2-methyl-butyric acid methyl ester (0.23 g, 0.95 mmol) in tetrahydrofuran (3 ml) and the mixture was stirred for 2 hours. Sodium sulphate solution (2M, 0.3 ml) was added and the mixture was filtered through Celite. The solvent was evaporated and the residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/MeOH=95:5) to yield a colourless oil, (0.190 g, 93%);

Workup

  1. filtrationthe mixture was filtered through Celite
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/MeOH=95:5)
  4. customto yield a colourless oil, (0.190 g, 93%)

Sources & evidence

ORD record
ord-f925aa3216bc482f9d0a99fb96e82bf6
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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