1-Pentanethiol → 1-(Diphenylmethyl)-3-(pentylthio)azetidine

HRID 2172017Notes

Reaction equation

HRID 2172017 reaction equation
[CH2:1]([SH:6])[CH2:2][CH2:3][CH2:4][CH3:5].[H-].[Na+].CS(O[CH:14]1[CH2:17][N:16]([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15]1)(=O)=O.C([O-])(O)=O.[Na+]>CS(C)=O>[C:19]1([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:16]2[CH2:17][CH:14]([S:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:15]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 80671-PentanethiolHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 671546441-(Diphenylmethyl)-3-(pentylthio)azetidineYield 96%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of pentanethiol (248 μL, 2.0 mmol) in DMSO (2.5 mL) at 0° C. under nitrogen was added NaH (60% in oil, 80 mg, 2.0 mmol). The suspension was stirred for 0.5 h at 0° C. then treated with 1-(diphenylmethyl)azetidin-3-yl methanesulfonate (317 mg, 1.0 mmol; which may be prepared as described in Step 1) and the mixture allowed to warm to room temperature overnight. Saturated NaHCO3 (5 mL) was added and the mixture was extracted with diethyl ether. The organic layer was separated from the aqueous and the organic washed with brine, dried over Na2SO4 and concentrated to give the product (312 mg, 96%) as a yellow oil.

Workup

  1. temperatureto warm to room temperature overnight
  2. extractionthe mixture was extracted with diethyl ether
  3. customThe organic layer was separated from the aqueous and the
  4. washorganic washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9d4b79fb63ef444386ec8b84988e44b9
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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