Water → HCID 18689933, compound

HRID 1871921Notes

Reaction equation

HRID 1871921 reaction equation
[Cl-].[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[C:37]([O:41][C:42]([N:44]1[CH2:49][CH2:48][C:47](=O)[CH2:46][CH2:45]1)=[O:43])([CH3:40])([CH3:39])[CH3:38].O>C1COCC1>[C:37]([O:41][C:42]([N:44]1[CH2:49][CH2:48][C:47](=[CH:12][C:3]2[CH:4]=[CH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:2]=2)[CH2:46][CH2:45]1)=[O:43])([CH3:40])([CH3:38])[CH3:39]

Participants

6

Reactant 4

HCID 962WaterHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 22241267Triphenyl[(quinolin-2-yl)methyl]phosphanium chlorideHCID 178418339Butyllithium

Product 1

HCID 18689933HCID 18689933, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon, 2-quinolylmethyltriphenylphosphonium chloride (8.72 g) was dissolved in anhydrous THF (60 ml), and a 1.6N solution (15 ml) of butyllithium was added dropwise over 20 minutes under cooling on ice. The mixture was then stirred for 10 minutes at room temperature. To the mixture, an anhydrous THF (24 ml) solution of 1-tert-butoxycarbonyl-4-ketopiperidine (4.29 g) was added dropwise over 15 minutes under cooling on ice. The mixture was stirred for 30 minutes under cooling on ice and further stirred overnight at room temperature. Water (200 ml) was added to the reaction mixture, then the resultant mixture was extracted with ether. The organic phase was back-extracted with 1N hydrochloric acid, and the aqueous phase was neutralized with a saturated solution of sodium hydrogencarbonate. The resultant mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over sodium sulfate anhydrate, and concentrated under reduced pressure, to thereby obtain the title compound as a solid. This solid was used for subsequent reaction without further purification.

Workup

  1. temperatureunder cooling on ice
  2. temperatureunder cooling on ice
  3. stirringThe mixture was stirred for 30 minutes
  4. temperatureunder cooling on ice and further stirred overnight at room temperature
  5. extractionthe resultant mixture was extracted with ether
  6. extractionThe organic phase was back-extracted with 1N hydrochloric acid
  7. extractionThe resultant mixture was extracted with ethyl acetate
  8. washThe organic phase was washed with saturated brine
  9. dry with materialdried over sodium sulfate anhydrate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7eea003885d4a6bb244f16252590299
Source dataset
uspto-grants-2000_08
Patent number
US06107308

Reaction notes

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