Dimethyl Sulfide → HCID 66878012, compound

HRID 39022Notes

Reaction equation

HRID 39022 reaction equation
[CH2:1]([N:8]([CH2:11][C@@H:12]1[O:17][C:16]2[C:18]([F:22])=[CH:19][CH:20]=[CH:21][C:15]=2[O:14][CH2:13]1)[CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[CH3:28][S:29]C.[NH4+].[Cl-]>C1COCC1>[CH2:1]([N:8]([CH2:11][C@@H:12]1[O:17][C:16]2[C:18]([F:22])=[C:19]([S:29][CH3:28])[CH:20]=[CH:21][C:15]=2[O:14][CH2:13]1)[CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 25517Ammonium ChlorideHCID 66879064HCID 66879064, compoundHCID 178418339Butyllithium

Product 1

HCID 66878012HCID 66878012, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-75 °C

Procedure

A mixture of N-benzyl-N-{[(2S)-8-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}ethanamine (2.2 g, 7.3 mmol) and 2,2-tetramethylpiperidine (2.5 ml, 14.6 mmol) was added dropwise to n-BuLi (10 ml, 25 mmol) in THF (dry, 10 ml) under N2 at −75° C., followed by the addition of dimethylsulfide (1.32 ml, 14.6 mmol) in THF (dry, 10 ml). The mixture was stirred for 30 min at −75° C., and was then warmed to room temperature. NH4Cl (sat.) was added and the solution was extracted with EtOAc. The combined organic phases were washed with Na2SO3 (15%), brine, dried (Na2SO4) and evaporated to dryness. Flash column chromatography (isooctane/EtOAc) yielded the title compound (1.3 g). MS m/z (rel. intensity, 70 eV) 347 (2), 149 (12), 148 (100), 92 (7), 91 (92).

Workup

  1. temperaturewas then warmed to room temperature
  2. extractionthe solution was extracted with EtOAc
  3. washThe combined organic phases were washed with Na2SO3 (15%), brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-9c68bb1df5a142a18cd47b9c62088f29
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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