tert-Butyl (3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-3-hydroxypropyl)carbamate → tert-Butyl 2,4-dioxopiperidine-1-carboxylate

HRID 2365142Notes

Reaction equation

HRID 2365142 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][C:10](=[C:12]1C(=O)OC(C)(C)[O:14][C:13]1=O)[OH:11])([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1>[C:1]([O:5][C:6]([N:7]1[CH2:8][CH2:9][C:10](=[O:11])[CH2:12][C:13]1=[O:14])=[O:22])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 54704545tert-Butyl (3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-3-hydroxypropyl)carbamate

Product 1

HCID 23730999tert-Butyl 2,4-dioxopiperidine-1-carboxylateYield 102.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of [3-(2,2-dimethyl-4,6-dioxo-[1,3]dioxin-5-ylidene)-3-hydroxy-propyl]-carbamic acid tert-butyl ester (9.2 g, 29.2 mmol) obtained from Example 41 in 180 ml of dioxane was heated to reflux for 2 hours. The mixture was evaporated under reduced pressure to give the crude product 2,4-dioxo-piperidine-1-carboxylic acid tert-butyl ester (6.4 g) as a yellow oil which was used as such.

Workup

  1. temperatureto reflux for 2 hours
  2. customThe mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9a9b5132a12f4987a7fa3cdf69db722e
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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