Methanol → tert-Butyl 2,4-dioxopiperidine-1-carboxylate

HRID 1843982Notes

Reaction equation

HRID 1843982 reaction equation
CC1(C)OC(=O)[CH:5]([C:9](=[O:20])[CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:4](=O)[O:3]1.CO>C(OCC)(=O)C.C(Cl)Cl>[O:3]=[C:4]1[CH2:5][C:9](=[O:20])[CH2:10][CH2:11][N:12]1[C:13]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:19]

Participants

5

Reactant 2

HCID 887MethanolHCID 68556020tert-Butyl (3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3-oxopropyl)carbamate

Product 1

HCID 23730999tert-Butyl 2,4-dioxopiperidine-1-carboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

Tert-butyl 3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3-oxopropylcarbamate (I-59b: 50 g, 158.57 mmol) was dissolved in ethyl acetate (500 mL) at room temperature under nitrogen atmosphere and the resulting reaction mass was heated at 105° C. for 20 hours. The reaction was monitored by TLC (10% methanol in DCM). The reaction mass was cooled to room temperature and concentrated under reduced pressure to afford the crude product. Purification by ether-wash afforded 28 g of the product (83% yield).

Workup

  1. customthe resulting reaction mass
  2. temperatureThe reaction mass was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product
  5. customPurification by ether-
  6. washwash

Sources & evidence

ORD record
ord-d523c2a6945b4779912a904dc9b44fb0
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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