Chlorosulfonic acid → (R)-2-Butyl-2-ethylaziridine

HRID 1376408Notes

Reaction equation

HRID 1376408 reaction equation
ClS(O)(=O)=O.[NH2:6][C@:7]([CH2:14][CH3:15])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:8]O>ClC(Cl)C>[CH2:10]([C@:7]1([CH2:14][CH3:15])[CH2:8][NH:6]1)[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 15406632(R)-2-Amino-2-ethylhexan-1-OL

Product 1

HCID 53812986(R)-2-Butyl-2-ethylaziridineYield 77%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Chlorosulphonic acid (1 molar equivalent) was added to a solution of the product from step (f) (15 g) in dichloroethane (90 ml) at a temperature of <16° C. When addition was complete, the mixture was stirred for 2 hours at room temperature and then evaporated i vacuo. Water (60 ml) and 50% w/v aqu. NaOH (41 ml) were added and the mixture distilled at atmospheric pressure. The organic phase of the distillate was separated and dried over KOH to give a solution of the desired product (77% yield).

Workup

  1. additionWhen addition
  2. customevaporated i vacuo
  3. additionNaOH (41 ml) were added
  4. distillationthe mixture distilled at atmospheric pressure
  5. customThe organic phase of the distillate was separated
  6. dry with materialdried over KOH

Sources & evidence

ORD record
ord-7064ba60fd784219b47021f146fb0653
Source dataset
uspto-grants-1997_09
Patent number
US05663165

Reaction notes

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