Tetrabutylammonium Fluoride → HCID 22219940, compound

HRID 1794061Notes

Reaction equation

HRID 1794061 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:31])[S:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][Si](C(C)(C)C)(C)C)=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:31])[S:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22219880S-4-(tert-butyl-dimethylsilyloxy)benzyl 4-tert-butoxycarbonylpiperazine-1-thiocarboxylate

Product 1

HCID 22219940HCID 22219940, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

to a stirred solution of S-4-(tert-butyl-dimethylsilyloxy)benzyl 4-tert-butoxycarbonylpiperazine-1-thiocarboxylate (10 g, 22 mmol) in THF (100 mL) was added a solution of TBAF in THF (1 N, 24 mL, 24 mmol). The mixture was stirred at room temperature for 40 min then diluted with water (200 mL) and extracted with EtOAc (2×250 mL). The combined organic extracts were washed successively with water (250 mL) and brine (500 mL) then dried (MgSO4), filtered and concentrated to reveal a brown oil. Trituration with EtOAc/hexane afforded the product as a white solid (3.7 g, 47%): 1H-NMR (400 MHz, d6-DMSO) 9.32 (1H, m), 7.11 dt (2H, t, J 8.5, 2.5 Hz), 6.67 (2H, t, J 8.5, 2.5 Hz), 4.02 (2H, s), 3.43 (4H, m), 3.33 (4H, m) and 1.40 (9H, s).

Workup

  1. extractionextracted with EtOAc (2×250 mL)
  2. washThe combined organic extracts were washed successively with water (250 mL) and brine (500 mL)
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b6fff09c289340fb995d52ad4dd95e0d
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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