Chloroacetyl chloride → (1S)-1-(4-fluorophenyl)-2-(N-benzyl-N-chloroacetylamino)ethanol

HRID 1671474Notes

Reaction equation

HRID 1671474 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[F:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]([OH:23])[CH2:14][NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:9][CH:8]=1.[OH-].[Na+]>ClCCl>[F:6][C:7]1[CH:8]=[CH:9][C:10]([C@H:13]([OH:23])[CH2:14][N:15]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:3](=[O:4])[CH2:2][Cl:1])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 15983828(1S)-1-(4-fluorophenyl)-2-(benzylamino)ethanol

Product 1

HCID 67352707(1S)-1-(4-fluorophenyl)-2-(N-benzyl-N-chloroacetylamino)ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of chloroacetyl chloride (4.3 g, 3.4 ml, 38 mmol) in dichloromethane (20 ml) was added dropwise over 30 min to the ice-cooled mixture of a solution of (1S)-1-(4-fluorophenyl)-2-(benzylamino)ethanol (8.3 g, 34 mmol) in dichloromethane (100 ml) and 1N aqueous sodium hydroxide solution (40 ml, 40 mmol), and the mixture was stirred for 1 hr at same temperature. The resulting solution was washed successively with 0.5 M hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give (1S)-1-(4-fluorophenyl)-2-(N-benzyl-N-chloroacetylamino)ethanol. Potassium hydroxide (2.2 g, 39 mmol) was added to a solution of the obtained compound in isopropyl alcohol (60 ml), and the mixture was stirred for 4 hrs. The solvent was evaporated in vacuo and the residue was partitioned between water and ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give (6S)-6-(4-fluorophenyl)-4-(benzyl)morpholin-3-one (9.7 g) as a yellow oil.

Workup

  1. temperaturecooled
  2. washThe resulting solution was washed successively with 0.5 M hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d2c757f9af9041408ffbec52db781c93
Source dataset
uspto-grants-2011_08
Patent number
US07994315B2

Reaction notes

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