Water → HCID 86709386, compound

HRID 2172216Notes

Reaction equation

HRID 2172216 reaction equation
CC(C)([O-])C.[K+].C(OP([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)(=O)OCC)C.[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([CH2:39][CH:40]=O)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].O>O1CCCC1>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([CH2:39]/[CH:40]=[CH:15]/[C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:20][CH:21]=2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 10353694tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylateHCID 15819199Diethyl 4-(trifluoromethyl)benzylphosphonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86709386HCID 86709386, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Potassium tert-butoxide (5.78 g, 50.0 mmol) was added to a solution of 4-(trifluoromethyl)benzylphosphonic acid diethyl ester (14.8 g, 50.0 mmol) in tetrahydrofuran solution (40 ml) under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. Subsequently, a tetrahydrofuran solution (10 ml) of 4-(2-oxoethyl)piperidine-1-carboxylic acid tert-butyl ester (11.4 g, 50.0 mmol) was added thereto dropwise at 0° C., warmed to room temperature, and then stirred overnight. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. After filtering, the filtrate was concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=86:14) to afford the title compound as a colorless oil (8.6 g, yield 47%).

Workup

  1. stirringstirred overnight
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtering
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography (hexane:ethyl acetate=86:14)

Sources & evidence

ORD record
ord-bba9c38f91464741809bd0396a37673b
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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