Water → HCID 67099480, compound

HRID 858491Notes

Reaction equation

HRID 858491 reaction equation
C([O:5][C@H:6]([CH3:17])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)(=O)CC.[OH-].[Na+].O>C(O)C>[N+:14]([C:11]1[CH:10]=[CH:9][C:8]([CH2:7][C@H:6]([OH:5])[CH3:17])=[CH:13][CH:12]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67100124HCID 67100124, compound

Product 1

HCID 67099480HCID 67099480, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (1R)-1-methyl-2-(4-nitrophenyl)ethyl propanoate (step 1 of Example 248, 1.91 g, 8.05 mmol) in ethanol (20 ml) was added 2N aqueous NaOH (5 ml) at room temperature. The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was poured into water, extracted with diethyl ether (2×50 ml). The organic layer was washed with brine, dried (MgSO4), and concentrated. Purification by flash column chromatography eluting with hexane/diethyl ether (1:1) afforded 1.16 g (80%) of title compound as a colorless solid (79% e.e.). Recrystallization from hexane/diethyl ether afforded 717 mg of a colorless needle (99% e.e.).

Workup

  1. extractionextracted with diethyl ether (2×50 ml)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification by flash column chromatography
  6. washeluting with hexane/diethyl ether (1:1)

Sources & evidence

ORD record
ord-3bb909f229544e63a8bdc9b69f231694
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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