Sodium Hydroxide → tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

HRID 2407753Notes

Reaction equation

HRID 2407753 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[I-].[CH3:16][S+](C)(C)=O.[OH-].[Na+]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].C1(C)C=CC=CC=1.O>[O:1]1[C:2]2([CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH2:16]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylateYield 86.4%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of tert-butyl 4-oxopiperidine-1-carboxylate (2.00 g), trimethylsulfoxonium iodide (2.43 g) and tetrabutylammomium bromide (0.048 g) in toluene (20 mL) was added a solution of sodium hydroxide (5.02 mL) in water (6.3 mL) dropwise at room temperature. The resulting mixture was heated at 80° C. for 4 hours. The organic phase was separated and the aqueous layer was extracted with toluene. The combined extracts were washed with water, brine, dried and evaporated in vacuo and further dried under high vacuum to obtain the title compound (1.85 g) having the following physical data.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous layer was extracted with toluene
  3. washThe combined extracts were washed with water, brine
  4. customdried
  5. customevaporated in vacuo
  6. customfurther dried under high vacuum

Sources & evidence

ORD record
ord-241888d0afcb4ff29ff98b3a8ad40075
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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