Iodine → HCID 22975820, compound

HRID 514812Notes

Reaction equation

HRID 514812 reaction equation
Br[CH2:2][CH2:3][CH:4]=[CH2:5].[Mg].II.[O:9]=[C:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1>O1CCCC1.[Cl-].[NH4+]>[C:19]([O:18][C:16]([N:13]1[CH2:12][CH2:11][C:10]([CH2:5][CH2:4][CH:3]=[CH2:2])([OH:9])[CH2:15][CH2:14]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 807IodineHCID 21241Homoallyl bromideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5462224Magnesium

Product 1

HCID 22975820HCID 22975820, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

To a mixture of 4-bromobut-1-ene (10.9 g, 0.08 mol) and magnesium turnings (4.8 g, 0.2 mol) in dry tetrahydrofuran (80 mL) was added a crystal of iodine and the mixture was stirred at room temperature until complete reaction had occurred. To this mixture was added tert-butyl 4-oxopiperidine-1-carboxylate (7.7 g, 0.039 mol) in tetrahydrofuran (20 mL) at 0° C. After 1 h at 0° C., and 3 h at room temperature the reaction mixture was diluted with ammonium chloride solution and extracted with ethyl acetate. After drying over Na2SO4, the solvent was removed in vacuo and the residue was purified via flash chromatography with 25% ethyl acetate/hexane to afford the title compound 16B (3.63 g) as an oil. 1H NMR (CHLOROFORM-d) δ 5.84 (d, J=6.7 Hz, 1H), 4.89-5.11 (m, 2H), 3.16 (br. s., 2H), 2.16 (d, J=9.4 Hz, 2H), 1.48-1.66 (m, 6H), 1.45 (s, 9H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialAfter drying over Na2SO4
  3. customthe solvent was removed in vacuo
  4. customthe residue was purified via flash chromatography with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-33f31bd005614aaf841135b4a0ebda3a
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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