Water → HCID 86594844, compound

HRID 859918Notes

Reaction equation

HRID 859918 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[N:11][CH:12]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[C:6]([C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)=[N:11][CH:12]=1)#[CH:5]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 69606761Tert-butyl 4-{5-[(trimethylsilyl)ethynyl]pyridin-2-yl}piperazine-1-carboxylate

Product 1

HCID 86594844HCID 86594844, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 4-{5-[(trimethylsilyl)ethynyl]pyridin-2-yl}piperazine-1-carboxylate (637 mg, 1.77 mmol), in THF (8 mL) at 25° C. was added tetrabutylammonium fluoride (1.77 mL, 1.0M in THF). The reaction was stirred for 1 hour. Water (5 mL) was then added and product extracted with ethyl acetate (2×5 mL). The combined organic extracts were then dried, (MgSO4), filtered and concentrated in vacuo to give tert-butyl 4-(5-ethynylpyridin-2-yl)piperazine-1-carboxylate as an orange solid (509 mg, 1.77 mmol, 100%).

Workup

  1. extractionproduct extracted with ethyl acetate (2×5 mL)
  2. dry with materialThe combined organic extracts were then dried, (MgSO4),
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29080fe439fd4da8b27031b6d5721378
Source dataset
uspto-grants-2006_12
Patent number
US07153857B2

Reaction notes

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