Ethanol → 3-(2-Chloro-4-methoxy-benzyl)-1-(4-fluoro-cyclohex-3-enyl)-pyrrolidin-2-one

HRID 1672721Notes

Reaction equation

HRID 1672721 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18](Cl)[C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]2)[C:6]1=[O:17].C(O)C.COCCN(S(F)(F)[F:38])CCOC>ClCCl>[Cl:1][C:2]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][C:13]([F:38])=[CH:12][CH2:11]2)[C:6]1=[O:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 578786063-(2,6-Dichloro-4-methoxy-benzyl)-1-(4-oxo-cyclohexyl)-pyrrolidin-2-one

Product 1

HCID 666974333-(2-Chloro-4-methoxy-benzyl)-1-(4-fluoro-cyclohex-3-enyl)-pyrrolidin-2-oneYield 35.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 3-(2,6-Dichloro-4-methoxybenzyl)-1-(4-oxocyclohexyl)-pyrrolidin-2-one (Preparation 17) (2.09 g, 5.4 mmol) in dichloromethane (50 mL) and ethanol (0.06 mL, 1.08 mmol) and cool to 0° C. Add deoxo-fluor (1.69 mL, 9.18 mmol) over several minutes. Stir overnight at room temperature. Add saturated sodium bicarbonate and extract aqueous layer with dichloromethane. Wash the organic layer with brine and dry with Na2SO4, filter and concentrate to dryness. Purify the crude mixture over silica gel (4/1 hexane in ethyl acetate) to give 650 mg (32%) of the title compound: mass spectrum (m/e): 374 (M+1).

Workup

  1. extractionAdd saturated sodium bicarbonate and extract aqueous layer with dichloromethane
  2. washWash the organic layer with brine
  3. dry with materialdry with Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate to dryness
  6. customPurify the crude mixture over silica gel (4/1 hexane in ethyl acetate)

Sources & evidence

ORD record
ord-f78c5062032a48518b4e50bf98f6af27
Source dataset
uspto-grants-2011_08
Patent number
US07998999B2

Reaction notes

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