1-Tert-butyl 3-methyl 4-(trifluoromethanesulfonyloxy)-1,2,5,6-tetrahydropyridine-1,3-dicarboxylate → HCID 58248373, compound

HRID 2039794Notes

Reaction equation

HRID 2039794 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[Mg]Cl.[CH3:10][O:11][C:12]([C:14]1[CH2:15][N:16]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:17][CH2:18][C:19]=1OS(C(F)(F)F)(=O)=O)=[O:13]>C1COCC1.[Cl-].[Zn+2].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:10][O:11][C:12]([C:14]1[CH2:15][N:16]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:17][CH2:18][C:19]=1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:9])=[O:13]

Participants

6

Reactant 2

HCID 152219361-Tert-butyl 3-methyl 4-(trifluoromethanesulfonyloxy)-1,2,5,6-tetrahydropyridine-1,3-dicarboxylateHCID 178424304HCID 178424304, compound

Product 1

HCID 58248373HCID 58248373, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

To a 1 M solution of o-tolylmagnesium chloride in THF (6.26 ml, 41.5 mmol) was added dropwise a freshly prepared solution of dried zinc chloride (8.48 g, 62.2 mmol) in dry THF (200 ml) at 0° C. After completed addition the reaction mixture was allowed to slowly warm to room temperature over a period of 1 h. To this mixture were added a solution of 4-trifluoromethanesulfonyloxy-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (10.7 g, 27.5 mmol) in THF (270 ml) and tetrakis(triphenylphosphine)palladium(0) (0.96 g, 0.83 mmol). After stirring for 6 h at room temperature the reaction was quenched with ice. The mixture was diluted with tert-butyl methyl ether and washed with 2 M aqueous sodium carbonate solution. The aqueous layer was extracted with two portions of tert-butyl methyl ether.

Workup

  1. additionaddition the reaction mixture
  2. customwas quenched with ice
  3. additionThe mixture was diluted with tert-butyl methyl ether
  4. washwashed with 2 M aqueous sodium carbonate solution
  5. extractionThe aqueous layer was extracted with two portions of tert-butyl methyl ether

Sources & evidence

ORD record
ord-0d83ffe18d414dfe929c061935d5993c
Source dataset
uspto-grants-2013_11
Patent number
US08580821B2

Reaction notes

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