Sodium Hydroxide → 1-Tert-butoxycarbonyl-2-methylpropyleneimine

HRID 350554Notes

Reaction equation

HRID 350554 reaction equation
C1(C)C=CC(S(OCC([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=O)(C)C)(=O)=O)=CC=1.[OH-].[Na+]>CCOCC>[C:19]([O:18][C:16](=[NH:15])[CH:20]=[C:19]([CH3:22])[CH3:21])([CH3:20])([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 235119882-Tert-butoxycarbonylamino-2-methyl-1-propyl p-toluenesulfonate

Product 1

HCID 865877951-Tert-butoxycarbonyl-2-methylpropyleneimineYield 145.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred mixture of 2-tert-butoxycarbonylamino-2-methyl-1-propyl p-toluenesulfonate (8.2 g, 23.88 mmol) and powdered NaOH (6.7 g, 0.151 mol) in Et2O (200 mL) was heated under reflux for 10 hr. After cooling, the mixture was filtered. And the filtrate was washed with water, brine, dried over Na2SO4, and evaporated. The residue was chromatographed on silica-gel with n-hexane:EtOAc (6:1 v/v) as eluent to give 2.7 g (66.2%) 1-tert-butoxycarbonyl-2-methylpropylene imine as an oil. 1H-NMR (CDCl3) δ 1.29 (s, 61H), 1.47 (s, 9H), 2.05 (s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hr
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. washAnd the filtrate was washed with water, brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue was chromatographed on silica-gel with n-hexane:EtOAc (6:1 v/v) as eluent

Sources & evidence

ORD record
ord-e1bcea51f6324eddb7178ae0f4113107
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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