Methanol → HCID 58275468, compound

HRID 42345Notes

Reaction equation

HRID 42345 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[C:11]([CH3:17])[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][Mg+].[Br-].CO.[BH4-].[Na+]>C1COCC1>[NH2:16][CH:15]([C:12]1[CH:13]=[CH:14][C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:8])=[O:7])=[CH:10][C:11]=1[CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 58275375HCID 58275375, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 58275468HCID 58275468, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N-tert-butyl-4-cyano-3-methylbenzenesulfonamide (0.4861 g) in THF (19 ml) at 0° C. was treated with MeMgBr (1.4 M in THF, 4.13 ml). The reaction mixture was heated at reflux overnight. After cooling, the reaction was quenched with MeOH and sodium borohydride (3 eq) was added. The mixture was stirred at 0° C. for 1 h, warmed to room temperature and stirred for 4 hours. The reaction mixture was then quenched with H2O, stirred overnight and concentrated to give a yellow solid. The solid was partitioned between EtOAc/H2O and the organic layer was separated, dried (MgSO4) and concentrated to give a yellow oil. The oil was purified by reverse phase HPLC (5-100% ACN/H2O+0.1% TFA) to give 0.3403 g 4-(1-aminoethyl)-N-tert-butyl-3-methylbenzenesulfonamide as white powder after lyophilization.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. additionwas added
  5. temperaturewarmed to room temperature
  6. stirringstirred for 4 hours
  7. customThe reaction mixture was then quenched with H2O
  8. stirringstirred overnight
  9. concentrationconcentrated
  10. customto give a yellow solid
  11. customThe solid was partitioned between EtOAc/H2O
  12. customthe organic layer was separated
  13. dry with materialdried (MgSO4)
  14. concentrationconcentrated
  15. customto give a yellow oil
  16. customThe oil was purified by reverse phase HPLC (5-100% ACN/H2O+0.1% TFA)

Sources & evidence

ORD record
ord-294e60a5d2ab46a994eb0cb821346119
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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