Dichloromethane → HCID 59597454, compound

HRID 2384556Notes

Reaction equation

HRID 2384556 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C@:9]23[CH2:14][C@H:13]2[CH2:12][N:11]([CH:15]([CH3:19])[CH2:16][CH2:17]O)[CH2:10]3)=[CH:5][CH:4]=1.S(Cl)([Cl:24])=O.[OH-].[Na+].ClCCl>C(Cl)(Cl)Cl>[Cl:24][CH2:17][CH2:16][CH:15]([N:11]1[CH2:12][C@H:13]2[C@:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:21])([F:20])[F:1])=[CH:4][CH:5]=3)([CH2:14]2)[CH2:10]1)[CH3:19]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 60135625HCID 60135625, compound

Product 1

HCID 59597454HCID 59597454, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}-1-butanol (Preparation 19, 130 mg) in chloroform (4 mL), thionyl chloride (0.87 mmol) was added and the mixture was stirred at room temperature for 6 h. After addition of NaOH (1 M), dichloromethane was added and the organic layer was washed with Brine and dried over Na2SO4. The solution was concentrated in vacuo and the crude product purified by flash chromatography (ethyl acetate:cyclohexane=5:95) to give 106 mg of the title compound.

Workup

  1. additionwas added
  2. washthe organic layer was washed with Brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe solution was concentrated in vacuo
  5. customthe crude product purified by flash chromatography (ethyl acetate:cyclohexane=5:95)

Sources & evidence

ORD record
ord-4801c000cfed4503806ca81608377381
Source dataset
uspto-grants-2012_09
Patent number
US08263782B2

Reaction notes

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