Water → 1,1-Dimethylethyl 2-(hydroxymethyl)-1-oxa-7-azaspiro[3.5]nonane-7-carboxylate

HRID 1059331Notes

Reaction equation

HRID 1059331 reaction equation
[O:1]1[CH2:18][CH:2]1[CH2:3][C:4]1([OH:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.O.[OH-].[Li+].C(OCC)(=O)C>CS(C)=O>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][C:4]2([O:17][CH:2]([CH2:18][OH:1])[CH2:3]2)[CH2:5][CH2:6]1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 186702981,1-Dimethylethyl 4-hydroxy-4-(2-oxiranylmethyl)-1-piperidinecarboxylate

Product 1

HCID 186703571,1-Dimethylethyl 2-(hydroxymethyl)-1-oxa-7-azaspiro[3.5]nonane-7-carboxylateYield 23.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1.42 g of 4-(2,3-epoxypropan-1-yl)-1-(tert-butoxycarbonyl)piperidin-4-ol in dimethyl sulfoxide (20 ml) were added in a nitrogen atmosphere 5 ml of water and 2.32 g of lithium hydroxide and the resulting mixture was heated to 140° C. for 30 minutes. After adding ethyl acetate, the reaction mixture was washed with water thrice. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with dichloromethane/ethyl acetate) to thereby give 0.336 g of the title compound as colorless crystals.

Workup

  1. washthe reaction mixture was washed with water thrice
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluted with dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-3224258e2c0e4c2791b53ce434366175
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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