Carbon Dioxide → HCID 59495804, compound

HRID 219873

Reaction equation

HRID 219873 reaction equation
C([Li])(C)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH3:19])=[C:9]([CH2:20][O:21][CH3:22])[CH:8]=1.[C:23](=[O:25])=[O:24]>CCOCC.CCOCC.CCOC(C)=O.O>[CH3:22][O:21][CH2:20][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH3:19])[C:23]([OH:25])=[O:24]

Participants

7

Reactant 3

HCID 280Carbon DioxideHCID 585541231-(4-Bromo-2-(methoxymethyl)phenyl)-2-methylpiperidineHCID 178418306HCID 178418306, compound

Product 1

HCID 59495804HCID 59495804, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 21584169Diethylether ethylacetateSolvent

Procedure

To anhydrous Et2O (130 mL) at −78° C. was added tert-butyllithium (63.79 mL; 1.50 M; 95.68 mmol) (solution in pentane) which was followed by the slow addition of a solution of 1-[4-bromo-2-(methoxymethyl)phenyl]-2-methylpiperidine (12.97 g; 43.49 mmol) in anhydrous Et2O (20 mL). After 40 min, the reaction mixture was poured on an excess of freshly crushed dry ice and stirred for 30 min after which time it was diluted with Et2O/EtOAc (1:1, 800 mL), water (200 mL, pH 4-5). The organic layers were combined, dried over MgSO4 and the solvents were removed under reduced pressure to give a yellow oil that was triturated in iPr2O (˜20 mL) and pentane (˜20 mL), filtered off and washed with pentane to give the title compound as a beige powder. LC/MS (Method B): 264.1 (M+H)+.

Workup

  1. dry with materialdried over MgSO4
  2. customthe solvents were removed under reduced pressure
  3. customto give a yellow oil that
  4. customwas triturated in iPr2O (˜20 mL)
  5. filtrationpentane (˜20 mL), filtered off
  6. washwashed with pentane

Sources & evidence

ORD record
ord-936a0edee15149f29d462b20cd920a2f
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Linked notes

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