tert-Butyl 3-(3-oxopropyl)piperidine-1-carboxylate → HCID 58091385, compound

HRID 2045694Notes

Reaction equation

HRID 2045694 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].O=CCC[CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:2]([CH:14]1[CH2:15][CH2:10][CH2:11][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]1)[CH2:3][CH:4]=[CH2:5]

Participants

5

Reactant 2

HCID 58091405tert-Butyl 3-(3-oxopropyl)piperidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 58091385HCID 58091385, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

A 1 L oven-dried round-bottom flask was charged with methyltriphenylphosphonium bromide (9.30 g, 26.0 mmol) and THF (250 mL) and cooled to −70° C. A solution of BuLi (2.5 M in hexanes, 10.4 mL, 26.0 mmol) was added dropwise, and the reaction mixture was stirred for 1 h. A solution of tert-butyl 3-(3-oxopropyl)piperidine-1-carboxylate (4.19 g, 17.4 mmol) in THF (15 mL) was added, and the reaction mixture was slowly warmed to RT and stirred for 3 days. The reaction mixture was quenched with water and concentrated to remove THF. The mixture was extracted with EtOAc and the combined organic layers were washed with brine, dried with anhydrous MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography (95 hexane/5 EtOAc) to give the title compound as a colorless oil. 1H NMR (CDCl3): δ 5.83-5.77 (m, 1H), 5.0{tilde over (4)} 4.95 (m, 2H), 3.9{tilde over (2)} 3.88 (m, 2H), 2.77 (s, br, 1H)), 2.6{tilde over (0)} 2.35 (m, 1H), 2.1{tilde over (1)} 2.07 (m, 2H), 1.81 (m, 1H), 1.6{tilde over (4)} 1.58 (m, 1H), 1.5{tilde over (0)} 1.20 (m, 13H), 1.2{tilde over (5)} 1.00 (m, 1H) ppm.

Workup

  1. temperaturethe reaction mixture was slowly warmed to RT
  2. stirringstirred for 3 days
  3. customThe reaction mixture was quenched with water
  4. concentrationconcentrated
  5. customto remove THF
  6. extractionThe mixture was extracted with EtOAc
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried with anhydrous MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel chromatography (95 hexane/5 EtOAc)

Sources & evidence

ORD record
ord-51cc1dec0c3644a3bbce87efe9915cb4
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

Loading…