Tetrabutylammonium Fluoride → tert-Butyl 4-((6-(hydroxymethyl)pyridin-2-yl)oxy)piperidine-1-carboxylate

HRID 2239361Notes

Reaction equation

HRID 2239361 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:15]=[C:14]([O:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[CH:13]=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH2:9][C:10]1[N:15]=[C:14]([O:16][CH:17]2[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68709259tert-Butyl 4-{[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]oxy}piperidine-1-carboxylate

Product 1

HCID 86618690tert-Butyl 4-((6-(hydroxymethyl)pyridin-2-yl)oxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-{[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]oxy}piperidine-1-carboxylate (0.50 g, 1.18 mmol) in THF (8 mL) was added tetrabutylammonium fluoride (1.78 mL, 1.0 M in THF, 1.78 mmol). The resulting mixture was stirred at room temperature for 1 hour, concentrated and purified by flash chromatography using a gradient run from 5-100% EtOAc in toluene. The selected fractions were concentrated in vacuo to give the product as a clear oil. Yield: 0.34 g (93%). 1H NMR (400 MHz, CDCl3) δ 7.54 (t, 1H, J=7.66 Hz), 6.78 (d, 1H, J=7.26 Hz), 6.59 (d, 1H, J=8.16 Hz), 5.15-5.26 (m, 1H), 4.62 (s, 2H), 3.66-3.77 (m, 2H), 3.25-3.37 (m, 3H), 1.89-1.99 (m, 2H), 1.59-1.82 (m, 2H), 1.45 (s, 9H).

Workup

  1. concentrationconcentrated
  2. custompurified by flash chromatography
  3. concentrationThe selected fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-4f50cd98018f45d68308b76400e5d4f4
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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