Dimethylformamide → HCID 90419088, compound

HRID 514814Notes

Reaction equation

HRID 514814 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([O:18][C:19](=[O:21])[CH3:20])([CH2:14][CH2:15][CH:16]=[CH2:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C=[O:26])C>O.Cl[Cu].Cl[Pd]Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([O:18][C:19](=[O:21])[CH3:20])([CH2:14][CH2:15][C:16](=[O:26])[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 90419163HCID 90419163, compound

Product 1

HCID 90419088HCID 90419088, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent

Procedure

To a solution of tert-butyl-4-acetoxy-4-(but-3-en-1-yl)piperidine-1-carboxylate (1 g, 3.36 mmol) in DMF (6 mL) and H2O (2 mL) was added CuCl (0.77 g, 7.73 mmol) and PdCl2 (0.16 g, 0.91 mmol) and the resulting suspension was stirred under an oxygen atmosphere at room temperature for 24 h. The insoluble materials were removed by filtration, and washed with ethyl acetate. The filtrate was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to give 16D (540 mg) as a colorless oil. 1H NMR (CHLOROFORM-d) δ: 3.84 (br. s., 2H), 2.97 (t, J=12.1 Hz, 2H), 2.38-2.47 (m, 2H), 2.17-2.24 (m, 2H), 2.15 (s, 3H), 2.04 (s, 3H), 1.39-1.51 (m, 9H).

Workup

  1. customThe insoluble materials were removed by filtration
  2. washwashed with ethyl acetate
  3. dry with materialThe filtrate was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-67fae75a567d4ac4b0aafd14577b330f
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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