Potassium hydride → HCID 66968168, compound

HRID 2077366Notes

Reaction equation

HRID 2077366 reaction equation
[H-].[K+].Br[C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.C([Li])CCC.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[C:32](=[O:37])N(OC)C)=[O:25])([CH3:22])([CH3:21])[CH3:20]>C1COCC1>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[C:32]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)=[O:37])=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 82127Potassium hydrideHCID 27627562-BromoquinolineHCID 21988510tert-Butyl 2-(methoxy(methyl)carbamoyl)piperidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 66968168HCID 66968168, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

30% Potassium hydride dispersed in mineral oil (0.8 g, 6 mmol) was added to a stirred solution of 2-bromoquinoline (1.12 g, 5.29 mmol) (O. Sugimoto, Tet. Lett. 4, (1999), 7477-8) in anhydrous THF (20 ml) at −70° C. under argon. To this was added 2N n-butyllithium in hexanes (2.7 ml, 6.75 mmol) dropwise over 5 min. The resultant mixture was stirred for 10 min at −70° C. then a solution of (RS)-1-(tert-butyloxycarbonyl)-2-(N-methoxy-N-methylcarbamoyl)-piperidine, D1 (1.57 g, 5.77 mmol) in anhydrous THF (10 ml) was added over 2 min. The cooling bath was removed and the reaction mixture allowed to warm to −20° C. and held at −20° C. for 10 min. The mixture was poured into saturated ammonium chloride (300 ml) and extracted with ethyl actetate (2×100 ml). The combined organics were dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 0-10% ethyl acetate in pentane to yield the title compound as a pale yellow solid (1.2 g, 66%).

Workup

  1. customat −70° C.
  2. customThe cooling bath was removed
  3. additionThe mixture was poured into saturated ammonium chloride (300 ml)
  4. extractionextracted with ethyl actetate (2×100 ml)
  5. dry with materialThe combined organics were dried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with 0-10% ethyl acetate in pentane

Sources & evidence

ORD record
ord-1abe8050fd6b4a19bd6257b71f4ab46e
Source dataset
uspto-grants-2011_04
Patent number
US07928125B2

Reaction notes

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