Diisopropylamine → HCID 22484973, compound

HRID 1368219Notes

Reaction equation

HRID 1368219 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].Br[CH2:23][CH2:24][CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>O1CCCC1.CCCCCC>[C:13]([NH:17][S:18]([CH2:21][CH2:23][CH2:24][CH2:25][O:26][Si:27]([C:30]([CH3:31])([CH3:33])[CH3:32])([CH3:28])[CH3:29])(=[O:20])=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 4130162N-tert-butylmethanesulfonamideHCID 178418339Butyllithium

Product 1

HCID 22484973HCID 22484973, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of diisopropylamine (3.7 ml) in tetrahydrofuran (18 ml) was added dropwise a 1.6 M solution (15 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-butylmethanesulfonamide(3.63 g) in tetrahydrofuran (12 ml) was added dropwise at an inside temperature of from −63° C. to −59° C. over 5 minutes. After stirring for 1 hr under ice-cooling, the mixture was cooled to an inner temperature of −60° C. again. 1-Bromo-3-(tert-butyldimethylsilyloxy)propane (3.35 ml) was added dropwise and the mixture was stirred overnight at room temperature. The reaction mixture was partitioned between ethyl acetate and saturated brine and the organic layer was dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1) to give N-tert-butyl-4-(tert-butyl-dimethylsilyloxy)butanesulfonamide (618 mg) as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 1 hr under ice-
  3. temperaturecooling
  4. stirringthe mixture was stirred overnight at room temperature
  5. customThe reaction mixture was partitioned between ethyl acetate and saturated brine
  6. dry with materialthe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-86e00da9acf1486ca12c618638b39ec6
Source dataset
uspto-grants-2003_06
Patent number
US06573274B1

Reaction notes

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