Sodium borohydride → HCID 69006324, compound

HRID 1436088Notes

Reaction equation

HRID 1436088 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([NH:12][CH2:13][C:14](=[O:16])[CH3:15])[CH3:11])=[CH:6][CH:5]=1>C(O)C.C(OCC)(=O)C>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]([NH:12][CH2:13][CH:14]([OH:16])[CH3:15])[CH3:11])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 69006026HCID 69006026, compound

Product 1

HCID 69006324HCID 69006324, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (2.39 g) was added to a solution of 1-[(S)-1-(4-fluorophenyl)ethylamino]propan-2-one (2.5 g) in ethanol (25 mL) under ice-cooling, and then the reaction solution was stirred at room temperature for one hour. The reaction solution was diluted with ice water and ethyl acetate, and then the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography using a silica gel (chloroform:2-propanol=100:1 to 0:100) to obtain 1.18 g of the title compound as a diastereomer mixture.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-76ea38a5624742a9aabdf90917aaa96f
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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