Sodium Hydroxide → 1,1-Dimethylethyl 4-[5-(hydroxymethyl)-1,2,4-oxadiazol-3-yl]piperazine-1-carboxylate

HRID 2199686Notes

Reaction equation

HRID 2199686 reaction equation
C([O:4][CH2:5][C:6]1[O:10][N:9]=[C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[N:7]=1)(=O)C.[OH-].[Na+]>CO>[OH:4][CH2:5][C:6]1[O:10][N:9]=[C:8]([N:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]2)[N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 668385551,1-Dimethylethyl 4-{5-[(acetoxy)methyl]-1,2,4-oxadiazol-3-yl}piperazine-1-carboxylate

Product 1

HCID 666729771,1-Dimethylethyl 4-[5-(hydroxymethyl)-1,2,4-oxadiazol-3-yl]piperazine-1-carboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,1-Dimethylethyl 4-{5-[(acetoxy)methyl]-1,2,4-oxadiazol-3-yl}piperazine-1-carboxylate (13.57 g, 41.6 mmol) was dissolved in methanol (100 mL) followed by addition of aqueous sodium hydroxide (4M, 10.4 mL) and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was then concentrated in vacuo and the residue partitioned with ethyl acetate and 0.1M aqueous hydrochloric acid. The organic layer was then washed with saturated aqueous sodium chloride then dried over anhydrous magnesium sulfate. Filtration and concentration afforded 1,1-dimethylethyl 4-[5-(hydroxymethyl)-1,2,4-oxadiazol-3-yl]piperazine-1-carboxylate (10.51 g, 89% yield) as a colorless crystalline solid. 1H-NMR (400 MHz, CDCl3): 4.75 (s, 2H), 3.53-3.50 (m, 4H), 3.44-3.42 (m, 4H), 3.20 (br s, 1H), 1.48 (s, 9H).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue partitioned with ethyl acetate and 0.1M aqueous hydrochloric acid
  3. washThe organic layer was then washed with saturated aqueous sodium chloride
  4. dry with materialthen dried over anhydrous magnesium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-6776caf8f3d445be85cc92a634c58343
Source dataset
uspto-grants-2016_06
Patent number
US09359332B2

Reaction notes

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