Diisopropylamine → N-(1,1-Dimethylethyl)-β-hydroxy-4-pyridineethanesulfonamide

HRID 2181008Notes

Reaction equation

HRID 2181008 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])([CH3:16])([CH3:15])[CH3:14].[CH:22]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)=[O:23]>O1CCCC1.CCCCCC.O>[C:13]([NH:17][S:18]([CH2:21][CH:22]([OH:23])[C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)(=[O:20])=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 133894-PyridinecarboxaldehydeHCID 4130162N-tert-butylmethanesulfonamideHCID 178418339Butyllithium

Product 1

HCID 22485068N-(1,1-Dimethylethyl)-β-hydroxy-4-pyridineethanesulfonamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of diisopropylamine (7.4 ml) in tetrahydro-furan (36 ml) was added dropwise a 1.6 M solution (30 ml) of 1-butyllithium in n-hexane under a nitrogen atmosphere at an inside temperature of from −62° C. to −48° C. over 5 minutes. After stirring for 30 min under ice-cooling, a solution of N-tert-butylmethane-sulfonamide (3.63 g) in tetrahydrofuran (15 ml) was added dropwise at an inside temperature of from −60° C. to −50° C. over 5 minutes. After stirring for 1 hr under ice-cooling, the mixture was cooled to an inner temperature of −60° C. again. 4-Formyl-pyridine (2.74 ml) was added dropwise and after stirring at room temperature for 5 hr, the mixture was left standing overnight. Water (250 ml) was gradually added to the reaction mixture under ice-cooling, and the mixture was extracted 4 times with ethyl acetate. The organic layers were combined and dried over magnesium sulfate and concentrated to dryness under reduced pressure to give N-tert-butyl-2-hydroxy-2-(4-pyridyl)ethane-sulfonamide (7.02 g) as a brown oil.

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 1 hr under ice-
  3. temperaturecooling
  4. stirringafter stirring at room temperature for 5 hr
  5. waitthe mixture was left
  6. waitstanding overnight
  7. temperaturecooling
  8. extractionthe mixture was extracted 4 times with ethyl acetate
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a22e531a217e4cec888aadb421be84a4
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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