Water → 1-p-Toluenesulfonyl-2(r)-ethylaziridine

HRID 2303980Notes

Reaction equation

HRID 2303980 reaction equation
[CH3:1][CH2:2][CH:3]([NH2:6])[CH2:4]O.[OH-].[Na+].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.O>COC(C)(C)C>[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15]([N:6]2[CH2:4][C@H:3]2[CH2:2][CH3:1])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 221292-Amino-1-butanol

Product 1

HCID 110096371-p-Toluenesulfonyl-2(r)-ethylaziridine

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Conditions

Temperature
25 °C

Procedure

R-(−)-2-amino-1-butanol (99.96 g, 105 mL) and tert-butyl methyl ether (TBME) (277 g, 366 mL) are combined under a nitrogen atmosphere. This mixture is stirred for several minutes and 10 N aqueous sodium hydroxide (449 mL) is added over a period of about 10 minutes. The reaction mixture is cooled to below 10° C. and a solution of p-toluene sulfonyl chloride (TsCl) (464 g) in TBME (711 g) is added over a period of about 50 minutes, maintaining the temperature of the reaction mixture at or below 32° C. After the addition is complete, the mixture is stirred for about 30 minutes at 40° C., and water (900 mL) is added while cooling the mixture to 25° C. The layers are separated and the organic layer washed sequentially with water (150 g) and 25% aqueous sodium chloride solution (300 g). Toluene (450 g) is added to the organic layer, and the mixture distilled under reduced pressure, maintaining the temperature of the mixture at or below 45° C., until the water content of the mixture is below about 0.1%. The resulting solution is used, without further treatment, for the preparation described in Example 2.

Workup

  1. temperatureThe reaction mixture is cooled to below 10° C.
  2. temperaturemaintaining the temperature of the reaction mixture at or below 32° C
  3. additionAfter the addition
  4. stirringthe mixture is stirred for about 30 minutes at 40° C.
  5. customThe layers are separated
  6. washthe organic layer washed sequentially with water (150 g) and 25% aqueous sodium chloride solution (300 g)
  7. additionToluene (450 g) is added to the organic layer
  8. distillationthe mixture distilled under reduced pressure
  9. temperaturemaintaining the temperature of the mixture at or below 45° C.

Sources & evidence

ORD record
ord-767678e1701641d28b66beb8adacdeea
Source dataset
uspto-grants-2002_08
Patent number
US06433172B1

Reaction notes

Loading…