Triethylamine → tert-butyl-3-(N'-hydroxycarbamimidoyl)morpholine-4-carboxylate

HRID 2114762Notes

Reaction equation

HRID 2114762 reaction equation
[C:1]([CH:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])#[N:2].Cl.[NH2:17][OH:18].C(N(CC)CC)C>CCO>[NH2:2]/[C:1](=[N:17]\[OH:18])/[CH:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 21098190tert-Butyl 3-cyanomorpholine-4-carboxylate

Product 1

HCID 21098191tert-butyl-3-(N'-hydroxycarbamimidoyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of Step 3 (1 eq.), hydroxylamine hydrochloride (1.4 eq.) and triethylamine (1.7 eq.) in EtOH (0.5 M) was refluxed under nitrogen for 5 hours. Mixture was concentrated and residues taken up in EtOAc and washed with water and brine. Combined organics were dried over Na2SO4 and evaporated giving the title compound as a yellow solid.

Workup

  1. concentrationMixture was concentrated
  2. washwashed with water and brine
  3. dry with materialCombined organics were dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-f24d70e8195a4c878714a8ef041262b6
Source dataset
uspto-grants-2008_10
Patent number
US07435734B2

Reaction notes

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