Dimethylformamide dimethyl acetal → 478623-90-4

HRID 2116612Notes

Reaction equation

HRID 2116612 reaction equation
[O:1]=[C:2]1[CH2:7][C:6](=[O:8])[CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.O(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O.CO[CH:33](OC)[N:34]([CH3:36])[CH3:35]>>[CH3:33][N:34]([CH:36]=[C:7]1[C:6](=[O:8])[CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][C:2]1=[O:1])[CH3:35]

Participants

4

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 90495Di-tert-butyl dicarbonateHCID 21942204tert-Butyl 3,5-dioxopiperidine-1-carboxylate

Product 1

HCID 68928249478623-90-4Yield 99%

Conditions

Temperature
80 °C

Procedure

56.0 g (of 1,1-dimethylethyl 3,5-dioxo-1-piperidinecarboxylate having the empirical formula C10H15NO4 (prepared by a method similar to that described in Heterocycles, 22, 2769-2773, (1984), replacing methyl chloroformate with (BOC)2O, are prepared as a suspension. 55.5 ml of N,N-dimethylformamide dimethyl acetal at 95% are added at room temperature. The medium is stirred for half an hour at 80° C. and then for 3 hours at 50° C. The solvent is evaporated off under reduced pressure. 79 g of 1,1-dimethylethyl 4-[(dimethylamino)methylene]-3,5-dioxo-1-piperidinecarboxylate having the empirical formula C13H20N2O4 are thus obtained. The corresponding yield is 99%.

Workup

  1. customare prepared as a suspension
  2. customThe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-9d93656102e340efbdcd4ace57f4c2e1
Source dataset
uspto-grants-2008_10
Patent number
US07439253B2

Reaction notes

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