Water → (R)-2-Amino-3-phenylsulfanyl-propan-1-ol

HRID 1911539Notes

Reaction equation

HRID 1911539 reaction equation
Cl.C[O:3][C:4](=O)[C@@H:5]([NH2:14])[CH2:6][S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:14][C@@H:5]([CH2:6][S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][OH:3]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68712569(R)-2-Amino-3-phenylsulfanyl-propionic acid methyl ester hydrochloride

Product 1

HCID 68714506(R)-2-Amino-3-phenylsulfanyl-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of (R)-2-amino-3-phenylsulfanyl-propionic acid methyl ester hydrochloride (0.50 g, 2.0 mmol) in tetrahydrofuran (10 ml) under an argon atmosphere was added slowly lithium aluminum hydride (0.153 g, 4.0 mmol) and the mixture was stirred overnight at room temperature. For work-up water (1.5 ml) and 2N sodium hydroxide solution (0.5 ml) were added and the mixture was stirred for 30 min. After filtration the solvent was evaporated and the residue was purified by column chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: heptane/EtOAc=1:1 to yield a light yellow oil, (0.095 g, 26%); MS (ISP): 183.9 ((M+H)+.).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. filtrationAfter filtration the solvent
  3. customwas evaporated
  4. customthe residue was purified by column chromatography (column
  5. customeluent: heptane/EtOAc=1:1 to yield a light yellow oil, (0.095 g, 26%)

Sources & evidence

ORD record
ord-7fcccd777cd842e9a32d73801cdcd41a
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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