Tetrahydrofuran → HCID 18442924, compound

HRID 458951Notes

Reaction equation

HRID 458951 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:11]([C:15]([O:17][N:18]1[CH2:23][CH2:22][CH:21]([C:24](=O)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:19]1)=[O:16])([CH3:14])([CH3:13])[CH3:12].C1C[O:35][CH2:34][CH2:33]1>>[C:25]1([CH:24]([CH:21]2[CH2:22][CH2:23][N:18]([O:17][C:15]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:16])[CH2:19][CH2:20]2)[CH2:33][CH:34]=[O:35])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 18442922HCID 18442922, compound

Product 1

HCID 18442924HCID 18442924, compound

Conditions

Temperature
0 °C

Procedure

To a solution of triethylphosphonoacetate (6.2 g, 27 mmol) in THF (100 mL) at 0° C. was added lithium bis(trimethylsilyl)amide (32.5 mL, 1M, 32.5 mmol). The resulting mixture was stirred at 0° C. for 20 min. 1-tert-Butylcarbonyloxy-4-benzoylpiperidine (7 g, 25 mmol) was added and the resulting mixture was stirred at room temperature for 48 h. The mixture was evaporated and the residue dissolved in ethyl acetate (200 mL). The solution was washed with 2M hydrochloric acid (2×100 mL), dried and evaporated giving the sub-titled compound.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 48 h
  2. customThe mixture was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate (200 mL)
  4. washThe solution was washed with 2M hydrochloric acid (2×100 mL)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-e7e1644fc0a04a87b86b2f1cae912284
Source dataset
uspto-grants-2007_03
Patent number
US07192973B2

Reaction notes

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