Tetrabutylammonium Fluoride → HCID 18423483, compound

HRID 1282015Notes

Reaction equation

HRID 1282015 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([O:18][CH2:19][CH2:20][CH2:21][O:22][Si](C(C)C)(C(C)C)C(C)C)([CH3:17])[CH3:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([O:18][CH2:19][CH2:20][CH2:21][OH:22])([CH3:16])[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18423423HCID 18423423, compound

Product 1

HCID 18423483HCID 18423483, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.245 g (0.52 mmol) of 1-t-butoxycarbonyl-4-(2-(3-triisopropylsilyloxy-1-propyl)oxy-2-methyl-1-propyl)piperidine and 0.53 mL (0.53 mmol) of tetrabutylammonium fluoride (TBAF) in 2 mL of THF was stirred at rt for 2 h. The reaction mixture was partitioned between ether and water. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:acetone, 9:1) to give the title compound.

Workup

  1. customThe reaction mixture was partitioned between ether and water
  2. washThe combined organic fractions were washed with sat'd NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (silica, hexanes:acetone, 9:1)

Sources & evidence

ORD record
ord-2141e785c460473a830f39639705d43c
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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