Tetrabutylammonium Fluoride → HCID 66731624, compound

HRID 1963117Notes

Reaction equation

HRID 1963117 reaction equation
[C:1]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][CH:10]2[CH2:15][CH:14]([CH2:16][O:17][Si](C(C)(C)C)(C)C)[CH2:13][CH2:12][N:11]2[C:25]([O:27][CH3:28])=[O:26])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][CH:10]2[CH2:15][CH:14]([CH2:16][OH:17])[CH2:13][CH2:12][N:11]2[C:25]([O:27][CH3:28])=[O:26])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66732334HCID 66732334, compound

Product 1

HCID 66731624HCID 66731624, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyl 2-(4-tert-butylbenzyl)-4-((tert-butyldimethylsilyloxy)methyl)-piperidine-1-carboxylate (6.27 g, 14.46 mmol) in tetrahydrofuran (15 mL) was added tetrabutylammonium fluoride (18.79 mL, 18.79 mmol, 1 M in THF) and the reaction mixture was stirred at room temperature for 90 minutes. The solvents were evaporated, the residue dissolved in ethyl acetate and washed with satd NaHCO3 (×1), then brine (×2). The organic layer was dried over MgSO4 and evaporated. The residue was purified by automated column chromatography (Biotage, (340 g KP-SIL) eluent EtOAc/heptane, gradient 20-90% EtOAc) to yield the product (3.21 g, 70%) as an oil. 1H NMR (400 MHz, cdcl3) δ 1.30 (s, 9H), 1.42-1.50 (m, 2H), 1.65-1.91 (m, 2H), 2.68 (m, 1H), 2.89-3.07 (m, 2H), 3.39-3.62 (m, 3H), 3.67 (m, 3H), 3.87 (m 1H), 4.07 (m, 1H), 7.11 (m, 2H), 7.30 (m, 2H). MS m/z 320 (M+H)+.

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with satd NaHCO3 (×1)
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated
  6. customThe residue was purified by automated column chromatography (Biotage, (340 g KP-SIL) eluent EtOAc/heptane, gradient 20-90% EtOAc)

Sources & evidence

ORD record
ord-644493f8d7fe4e00bb7e52869f3f7c31
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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