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

HRID 2065767
Notes
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Reaction equation

HRID 2065767 reaction equation
[Cl-].[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Zn+].C1(C)C=CC=CC=1[Mg]Cl.[CH3:19][O:20][C:21]([C:23]1[CH2:24][N:25]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:26][CH2:27][C:28]=1OS(C(F)(F)F)(=O)=O)=[O:22]>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>[CH3:19][O:20][C:21]([C:23]1[CH2:24][N:25]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:26][CH2:27][C:28]=1[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH3:2])=[O:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 152219361-Tert-butyl 3-methyl 4-(trifluoromethanesulfonyloxy)-1,2,5,6-tetrahydropyridine-1,3-dicarboxylateHCID 178424304HCID 178424304, compoundHCID 178424428HCID 178424428, compound

Product 1

HCID 58248373HCID 58248373, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalyst
HCID 178418397
HCID 178418397, compound
Catalyst
HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-methylphenylzinc chloride ([84109-17-1], previously prepared from o-tolylmagnesium chloride (44.07 mL) and zinc chloride (8.81 g) in THF (200 mL)) a mixture of 4-trifluoromethanesulfonyloxy-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (CAS Reg. No. [161491-25-4]) (11.4 g) in THF (90 mL) followed by tetrakis(triphenylphosphine)palladium(0) (1.02 g) was added. The reaction mixture was stirred at room temperature over night and then was quenched with ice. The mixture was diluted with tert-butyl methyl ether and washed with 2 M aqueous sodium carbonate solution. The aqueous phases were extracted with tert-butyl methyl ether. The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. Purification by chromatography (SiO2, n-heptane/ethyl acetate 5:1) gave 4-o-tolyl-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester as light yellow oil, MS: 332.0 ([M+H])+.

Workup

  1. additionwas added
  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 phases were extracted with tert-butyl methyl ether
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated
  10. customPurification by chromatography (SiO2, n-heptane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-6400119517dd4c2da4c2252f12abf657
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08288541B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes