Cyclopentanol → HCID 86722611, compound

HRID 2271500Notes

Reaction equation

HRID 2271500 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:15]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]2)CS(C)(=O)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:26]1([OH:31])[CH2:30][CH2:29][CH2:28][CH2:27]1>C(Cl)Cl>[CH:26]1([O:31][CH:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH:15]2[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:18]2)[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 7298CyclopentanolHCID 86722612HCID 86722612, compound

Product 1

HCID 86722611HCID 86722611, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tertiary butyl 3-(1-(3,4-dichlorophenyl)-2-(methylsulfonyl)ethyl)azetidine-1-carboxylate (0.2 g, 0.49 mmol) and cyclopentanol (3.0 mL, 2.4 mmol) were stirred at 80° C. for one day. The reaction mixture was dissolved in methylene chloride (70 mL), and the organic layer was washed with saturated sodium carbonate (Na2CO3) and distilled water once, respectively, and dried over anhydrous magnesium sulfate to remove the solvent. Finally, a colorless liquid was obtained, and purified by flash chromatography (n-hexane:ethyl acetate (2:1, v/v)). The product was identified as a single compound by TLC (n-hexane:ethyl acetate (2:1, v/v)).

Workup

  1. washthe organic layer was washed with saturated sodium carbonate (Na2CO3)
  2. distillationdistilled water once
  3. dry with materialrespectively, and dried over anhydrous magnesium sulfate
  4. customto remove the solvent
  5. customFinally, a colorless liquid was obtained
  6. custompurified by flash chromatography (n-hexane:ethyl acetate (2:1

Sources & evidence

ORD record
ord-6b94ec01010748d3a20c7b5739115746
Source dataset
uspto-grants-2015_09
Patent number
US09120771B2

Reaction notes

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