Potassium tert-butoxide → HCID 67505824, compound

HRID 473825Notes

Reaction equation

HRID 473825 reaction equation
[CH3:1]C(C)([O-])C.[K+].[F:7][C:8]1[CH:9]=[C:10]([CH:15]2[CH2:20][C:19](=O)[CH2:18][CH2:17][N:16]2[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH:11]=[CH:12][C:13]=1[F:14]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.CCCCCC>[F:7][C:8]1[CH:9]=[C:10]([CH:15]2[CH2:20][C:19](=[CH2:1])[CH2:18][CH2:17][N:16]2[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH:11]=[CH:12][C:13]=1[F:14]

Participants

6

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 67506327HCID 67506327, compound

Product 1

HCID 67505824HCID 67505824, compoundYield 79.3%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Potassium tert-butoxide (0.81 g, 7.2 mmol) was added to a suspension of methyltriphenylphosphonium bromide (2.58 g, 7.2 mmol) in tetrahydrofuran (20 mL) and the resulting mixture was stirred at room temperature for one hour. A solution of phenylmethyl 2-(3,4-difluorophenyl)-4-oxopiperidine-1-carboxylate (1.00 g, 2.9 mmol) (reagent preparation 20) in tetrahydrofuran (5 mL) was added and the resulting mixture was stirred at 35° C. for two hours. The mixture was cooled, diluted with hexane (100 mL), filtered, and the filtrate washed with water then brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (20% ethyl acetate in hexanes) to give phenylmethyl 2-(3,4-difluorophenyl)-4-methylidenepiperidine-1-carboxylate (0.79 g, 79% yield), MS (EI) for C20H19F2NO2: 344 (MH+).

Workup

  1. stirringthe resulting mixture was stirred at 35° C. for two hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe filtrate washed with water
  5. dry with materialbrine, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c5f374fbea474d34ab28589760dc228c
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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