Hexane → HCID 58017384, compound

HRID 451985Notes

Reaction equation

HRID 451985 reaction equation
BrC1C=CC=C(C)C=1.[Li]CCCC.CCCCCC.COC(NCC[O:27][C@@H:28]([C:42]1[CH:43]=[C:44]([CH3:48])[CH:45]=[CH:46][CH:47]=1)[C@@H:29]1[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]1)=O>C1COCC1>[CH3:48][C:44]1[CH:43]=[C:42]([CH:47]=[CH:46][CH:45]=1)[C:28]([C@@H:29]1[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:36])[CH2:30]1)=[O:27]

Participants

6

Reactant 4

HCID 8058HexaneHCID 115603-BromotolueneHCID 58017420HCID 58017420, compoundHCID 178418339Butyllithium

Product 1

HCID 58017384HCID 58017384, compoundYield 125.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-bromo-3-methylbenzene (88.4 g, 0.52 mol) in anhydrous THF (550 mL) at −78° C. under nitrogen was added dropwise a solution of 2.5 M n-BuLi in hexane (210 mL, 0.52 mol). After stirring for 1 hr at −78° C., a solution of (R)-tert-butyl 3-((R)-(2-(methoxycarbonylamino)ethoxy)(m-tolyl)methyl)piperidine-1-carboxylate (120 g, 0.44 mol) in anhydrous THF (500 mL) was added dropwise. After addition, the reaction mixture was allowed to warm to rt and stirred for 2 hr. The mixture was quenched with saturated NH4Cl solution (500 mL) and extracted with EtOAc (3×400 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give crude (R)-tert-butyl 3-(3-methylbenzoyl)piperidine-1-carboxylate (168 g), which was used immediately for next step without purification.

Workup

  1. additionAfter addition
  2. temperatureto warm to rt
  3. stirringstirred for 2 hr
  4. customThe mixture was quenched with saturated NH4Cl solution (500 mL)
  5. extractionextracted with EtOAc (3×400 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6fd14c6300a47d58d1d856b7aa0e0cf
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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