tert-Butanol → HCID 46253561, compound

HRID 1713109Notes

Reaction equation

HRID 1713109 reaction equation
Br.[N:2]1([C:8]([NH2:10])=[NH:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21](=O)[C:20](=[CH:25]N(C)C)[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].CC(C)([O-])C.[K+].C(O)(C)(C)C>CCO>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21]2[N:9]=[C:8]([N:2]3[CH2:7][CH2:6][O:5][CH2:4][CH2:3]3)[N:10]=[CH:25][C:20]=2[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 2806564Morpholine-4-carboximidamide HydrobromideHCID 23665647Potassium tert-butoxideHCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

Product 1

HCID 46253561HCID 46253561, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a 500 ml round bottom flask charged with anhydrous EtOH (150 ml) under nitrogen at 0° C. are added morpholine-4-carboxamidine hydrobromide (10.50 g, 50 mmol), tert-butyl-3-[(dimethylamino)methylene]-4-oxo-1-piperidinecarboxylate (12.7 g, 50 mmol, 1.0 eq.), and potassium t-butoxide in t-butanol (11.0M, 100 ml, 100 mmol, 2.0 eq.). The resulting mixture is stirred at 75° C. for 16 hr. The solvent is evaporated under reduced pressure, and the residue is taken up in DCM (300 ml), washed with water and brine, dried (Na2SO4) and concentrated. The residue is purified by silica gel chromatography (Hexane/EtOAc 1:1) to give the title compound. MS (+VE) m/z 321.1 (M++1).

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel chromatography (Hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-7a1b2c88050e4b0d8a190e35d0435036
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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