Sodium Sulfate → HCID 67179158, compound

HRID 1026106Notes

Reaction equation

HRID 1026106 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C@@H:11]([NH2:23])[CH2:12][CH2:13][C:14]([CH3:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])C.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[NH2:23][C@@H:11]([CH2:12][CH2:13][C:14]([CH3:22])([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH3:15])[CH2:10][OH:9]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 67177199HCID 67177199, compound

Product 1

HCID 67179158HCID 67179158, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (68 mg) in tetrahydrofuran (3 ml) was added a solution of (S)-2-amino-5-methyl-5-phenyl-hexanoic acid ethyl ester (280 mg) in tetrahydrofuran (1 ml) and the mixture was stirred for 3 hours at room temperature. Sodium sulphate solution (1N) was added until gas evolution ceased and the suspension was filtered through Celite. The solvent was evaporated and the residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: dichloromethane/MeOH=90:10) to yield a light yellow oil, (122 mg, 52%); MS (ISP): 208.2 ((M+H)+).

Workup

  1. filtrationthe suspension was filtered through Celite
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: dichloromethane/MeOH=90:10)
  4. customto yield a light yellow oil, (122 mg, 52%)

Sources & evidence

ORD record
ord-051dbddd241440b58aa9d22558a90c79
Source dataset
uspto-grants-2014_05
Patent number
US08729113B2

Reaction notes

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