(Dimethyl sulfide)trihydroboron → HCID 59394970, compound

HRID 1465160Notes

Reaction equation

HRID 1465160 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-:19])=[O:18])=[C:6]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=O)[CH:7]=1.CSC.B>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-:19])=[O:18])=[C:6]([CH2:8][CH2:9][N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[CH:7]=1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 59394964HCID 59394964, compound

Product 1

HCID 59394970HCID 59394970, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(5-Methyl-2-nitro-phenyl)-1-morpholino-ethanone (267 mg, 1.01 mmol) was dissolved in toluene (10 mL) and treated with borane dimethylsulfide (983 mg, 1.23 mL, 11.7 mmol) and heated at reflux for 2 h. The reaction was concentrated in vacuo then resuspended in 2 N HCl (8 mL) and heated at reflux for 30 min. The reaction was diluted with 1N HCl and washed with ethyl acetate. The solution was basified (5 N NaOH) and the product extracted into dichloromethane (3×20 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to provide 4-[2-(5-methyl-2-nitro-phenyl)ethyl]morpholine as an oil (200 mg, 79% yield). LC/MS m/z 251.2 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. concentrationThe reaction was concentrated in vacuo
  4. temperatureheated
  5. temperatureat reflux for 30 min
  6. additionThe reaction was diluted with 1N HCl
  7. washwashed with ethyl acetate
  8. extractionthe product extracted into dichloromethane (3×20 mL)
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a55079276c94502bda82cd07796eff7
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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