Hexane → HCID 66977242, compound

HRID 712215Notes

Reaction equation

HRID 712215 reaction equation
[N:1]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[Li+].CC([N-]C(C)C)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].CCCCCC>C1COCC1>[CH3:27][S:28]([C:4]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2][N:1]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:6][CH2:5]1)(=[O:30])=[O:29]

Participants

6

Reactant 4

HCID 8058HexaneHCID 31297Methanesulfonyl chlorideHCID 2724682Lithium diisopropylamideHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

Product 1

HCID 66977242HCID 66977242, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (2 g, 7.78 mmol) in THF (25 mL) was cooled to −78° C. followed by dropwise addition of LDA (1.8 M in THF, 8.8 mL, 15.56 mmol) and was stirred at the same temperature for 45 minutes followed by addition of methanesulfonyl chloride (1.3 g, 11.67 mmol) at −78° C. The temperature of the reaction was slowly raised to rt and left to stir for 6 h. The reaction was then cooled to 0° C. and quenched by drop wise addition of saturated NH4Cl solution (50 mL), extracted with EtOAc (3×100 mL) and the combined organics washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude residue was purified over 100-200 M silica-gel using 30% EtOAc:hexane to obtain the product as an orange viscous liquid (0.20 g, 8.0% yield). MS: 336.18 [M+H]+.

Workup

  1. waitleft
  2. stirringto stir for 6 h
  3. temperatureThe reaction was then cooled to 0° C.
  4. customquenched by drop wise addition of saturated NH4Cl solution (50 mL)
  5. extractionextracted with EtOAc (3×100 mL)
  6. washthe combined organics washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude residue was purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-078d4f500a5d4eef9552c793c79c99a7
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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