Triethylamine → 8-tert-Butyloxycarbonyl-2-methoxy-2,8-diazaspiro[4,5]decane-1,3-dione

HRID 1381943Notes

Reaction equation

HRID 1381943 reaction equation
Cl.[CH3:2][O:3][N:4]1[C:8](=[O:9])[CH2:7][C:6]2([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[C:5]1=[O:15].C(N(CC)CC)C.[C:23](OC([O-])=O)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>CN(C)C=O>[C:26]([O:25][C:23]([N:12]1[CH2:13][CH2:14][C:6]2([C:5](=[O:15])[N:4]([O:3][CH3:2])[C:8](=[O:9])[CH2:7]2)[CH2:10][CH2:11]1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 30882852,8-Diazaspiro(4,5)decane-1,3-dione, 2-methoxy-, monohydrochlorideHCID 22064466Tert-butyldicarbonate

Product 1

HCID 143718168-tert-Butyloxycarbonyl-2-methoxy-2,8-diazaspiro[4,5]decane-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methoxy-2,8-diazaspiro[4,5]decane-1,3-dione hydrochloride (1.5 g) in dimethylformamide (100 ml) was added triethylamine (1 ml), followed by tert-butyl dicarbonate (2.05 ml), and this was followed by stirring at room temperature for 1 hour. The solvent was evaporated off under reduced pressure. To the residual oil dichloromethane (50 ml) was added, after which it was washed with a 10% aqueous solution of citric acid, then with water. After drying the organic layer with anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The resulting residual solid was recrystallized with ethyl ether to obtain 1.4 g of a colorless crystal having a melting point of 117° C.

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. additionTo the residual oil dichloromethane (50 ml) was added
  3. washafter which it was washed with a 10% aqueous solution of citric acid
  4. dry with materialAfter drying the organic layer with anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residual solid was recrystallized with ethyl ether

Sources & evidence

ORD record
ord-365fe5725d1a447e86ca99febdd6a34b
Source dataset
uspto-grants-1989_02
Patent number
US04804665

Reaction notes

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