Tetrahydrofuran → HCID 18442924, compound

HRID 1434598Notes

Reaction equation

HRID 1434598 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-8d4fb4f55a49410a93cf5980566a0221
Source dataset
uspto-grants-2009_11
Patent number
US07615555B2

Reaction notes

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