Water → 1-(Diphenylmethyl)-3-(pentylsulfonyl)azetidine

HRID 2172018

Reaction equation

HRID 2172018 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:11][CH:10]([S:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:24]S(O)(=O)=O.OOS([O-])=O.[K+].C([O-])(O)=O.[Na+].[OH2:40]>CO>[C:18]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][CH:10]([S:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:24])=[O:40])[CH2:9]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 671546441-(Diphenylmethyl)-3-(pentylthio)azetidine

Product 1

HCID 671545941-(Diphenylmethyl)-3-(pentylsulfonyl)azetidineYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(diphenylmethyl)-3-(pentylthio)azetidine (228 mg, 0.70 mmol; which may be prepared as described in Step 2) in methanol (6.3 mL) and water (6.3 mL) was added H2SO4 1N (0.7 mL). The reaction mixture was stirred for 10 minutes, then oxone (1.08 g, 1.75 mmol) was added and the mixture stirred at room temperature for 12 h. A solution of saturated NaHCO3 (5 mL) was added and the mixture extracted with ethyl acetate. The two layers were separated and the organic washed with brine, dried over Na2SO4, filtered and concentrated. The crude was then purified on column chromatography (pentane/EtOAc, 100/0 then 90/10) to give the title product (75 mg, 30%) as a pale yellow oil. The less pure fraction (N-oxide) can be recycled in hydrogenolysis conditions.

Workup

  1. stirringthe mixture stirred at room temperature for 12 h
  2. extractionthe mixture extracted with ethyl acetate
  3. customThe two layers were separated
  4. washthe organic washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was then purified on column chromatography (pentane/EtOAc, 100/0

Sources & evidence

ORD record
ord-38c140669b834cb497824707375791fd
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Linked notes

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