tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 90412684, compound

HRID 1521962Notes

Reaction equation

HRID 1521962 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:9](I)=[CH:10][C:3]=12.C([Li])CCC.[O:27]=[C:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:9]([C:28]3([OH:27])[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])[CH2:32][CH2:33]3)=[CH:10][C:3]=12

Participants

5

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 224772394-Chloro-2-iodo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridineHCID 178418339Butyllithium

Product 1

HCID 90412684HCID 90412684, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (200 mg, 0.462 mmol) in tetrahydrofuran (1.5 mL) at −78° C. was added 1.6 M n-butyllithium in hexanes (0.347 mL, 0.555 mmol) under nitrogen. The mixture was stirred for 10 minutes and tert-butyl 4-oxopiperidine-1-carboxylate (111 mg, 0.555 mmol) was added. The mixture was stirred at −78° C. for 1 hour and was slowly warmed to room temperature overnight. The mixture was quenched with water, extracted with ethyl acetate (2×5 mL) and the organic layer was dried over magnesium sulfate, filtered, and concentrated. Purification by flash chromatography (silica gel, 20-100% ethyl acetate/heptanes) afforded the title compound. MS (ESI+) m/z 506.0 (M+H)+.

Workup

  1. stirringThe mixture was stirred at −78° C. for 1 hour
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate (2×5 mL)
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (silica gel, 20-100% ethyl acetate/heptanes)

Sources & evidence

ORD record
ord-94f17093b1624eb0a60e1483c0ccef11
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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