tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 69842491, compound

HRID 1059698Notes

Reaction equation

HRID 1059698 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([Li])CCC.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>O1CCCC1.CCCCCC>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27]([OH:30])([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 27627562-BromoquinolineHCID 178418339Butyllithium

Product 1

HCID 69842491HCID 69842491, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

A solution of 2-bromoquinoline (2.0 g, 9.61 mmol) in tetrahydrofuran (10 mL) was added dropwise to a mixture of n-butyllithium in hexane (4.2 mL of a 2.5 M solution) and tetrahydrofuran (10 mL) at −65° C. under N2, and the mixture was stirred at this temperature for 1 hour. A solution of t-butyl-4-oxo-1-piperidine carboxylate (1.92 g, 9.61 mmol) in tetrahydrofuran (10 niL) was added dropwise over 3 minutes., after the addition, the reaction was slowly warmed to ambient temperature and stirred for 16 hours. The reaction was quenched with sat. ammonium chloride (15 mL); the resulting mixture was stirred at ambient temperature for 10 minutes. The organic layer was separated, washed with water (20 mL), brine (20 mL), dried over magnesium sulfate. Concentration yielded 4-hydroxy-4-quinolin-2-yl-piperidine-1-carboxylic acid tert-butyl ester (3.16 g, 98%) as a yellow oil which was used without further purification. 1H NMR CDCl3 δ 8.20 (d, J=9 Hz, 1H), 8.08 (d, J=8 Hz, 1H), 7.83 (d, J=8 Hz, 1H), 7.73 (t, J=8 Hz, 1H), 7.55 (t, J=7 Hz, 1H), 7.42 (d, J=9 Hz, 1H), 5.94 (brd s, 1H), 4.23-4.00 (m, 2H), 3.70 (t, J=6 Hz, 1H), 3.40-3.22 (m, 2H), 2.42 (t, J=6 Hz, 1H), 2.13-1.98(m, 2H), 1.49 (s, 9H).

Workup

  1. addition, after the addition
  2. stirringstirred for 16 hours
  3. customThe reaction was quenched with sat. ammonium chloride (15 mL)
  4. stirringthe resulting mixture was stirred at ambient temperature for 10 minutes
  5. customThe organic layer was separated
  6. washwashed with water (20 mL), brine (20 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationConcentration

Sources & evidence

ORD record
ord-568695e78f364f07bf50c9ddc7a5bb17
Source dataset
uspto-grants-2003_02
Patent number
US06521630B1

Reaction notes

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