Potassium tert-butoxide → tert-Butyl 3,5-dioxopiperidine-1-carboxylate

HRID 2279473Notes

Reaction equation

HRID 2279473 reaction equation
CC(C)([O-])C.[K+].[C:7]([O:11][C:12]([N:14]([CH2:21][C:22](=[O:24])[CH3:23])[CH2:15][C:16](OCC)=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8]>CCOCC>[O:24]=[C:22]1[CH2:23][C:16](=[O:17])[CH2:15][N:14]([C:12]([O:11][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:13])[CH2:21]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 76849392HCID 76849392, compound

Product 1

HCID 21942204tert-Butyl 3,5-dioxopiperidine-1-carboxylateYield 60.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a cooled solution (0° C.) of potassium tert-butoxide (112.0 mL, 112.0 mmol) was added via addition funnel over 1.5 h, a solution 120 (26.41 g, 101.9 mmol) in ether (200 mL). The mixture was stirred for an additional 3 h. The precipitate was filtered off and washed with ether. The solid was dissolved in water and the pH was adjusted to ca. 4 with HOAc. The solids were filtered, washed with water, and dried to afford 13.16 g (60.6%) of tert-butyl 3,5-dioxopiperidine-1-carboxylate (122).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with ether
  3. dissolutionThe solid was dissolved in water
  4. filtrationThe solids were filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-1eda58aeb04d4f2abf5903ffc51bc01a
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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