Sodium hydride → HCID 68521328, compound

HRID 736660Notes

Reaction equation

HRID 736660 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8](P(OCC)(OCC)=O)[CH3:9])=[O:7].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][C:28](=O)[C:27](C)([CH3:32])[CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>C1COCC1>[CH2:4]([O:5][C:6](/[CH:8]=[C:9]1/[C:27]([CH3:28])([CH3:32])[CH2:26][N:25]([C:23]([O:22][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:24])[CH2:30][CH2:29]/1)=[O:7])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 107155Triethyl 2-phosphonopropionateHCID 22278899tert-Butyl 3,3-dimethyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 68521328HCID 68521328, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of NaH (0.212 g, 5.29 mmol) in THF (2 mL) was added a solution of triethyl 2-phosphonopropionate (1.05 mL, 5.29 mmol) in THF (2 mL) at 0° C. After the mixture was stirred for 1 h at rt, a solution of tert-butyl-3,3-dimethyl-4-oxopiperidine-1-carboxylate (J. Org. Chem., 2001, 66, 2487) (0.600 g, 2.64 mmol) in THF was then added and stirred for 10 h. The resulting mixture was quenched with water and the product portion was extracted with Et2O. The combined extracts were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography (gradient: 5% EtOAc/hexane to 40% EtOAc/hexane) to afford the titled compound (784 mg, ˜100%); 1H NMR (CDCl3) δ 5.73 (s, 1H), 4.15 (q, J=6.8 Hz, 2H), 3.52-3.42 (m, 2H), 3.25-3.18 (m, 2H), 3.05 (t, J=5.6 Hz, 2H), 1.47 (s, 9H), 1.29 (t, J=6.8 Hz, 3H), 1.12 (s, 6H)

Workup

  1. stirringstirred for 10 h
  2. customThe resulting mixture was quenched with water
  3. extractionthe product portion was extracted with Et2O
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by SiO2 chromatography (gradient: 5% EtOAc/hexane to 40% EtOAc/hexane)

Sources & evidence

ORD record
ord-e4b3778b6d0c44ad9412ac1a222293a4
Source dataset
uspto-grants-2009_09
Patent number
US07595401B2

Reaction notes

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