Tetrabutylammonium Fluoride → HCID 86618693, compound

HRID 2239367Notes

Reaction equation

HRID 2239367 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:15]=[C:14]([O:16][CH2:17][C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][N:19]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[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][CH2:17][C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][N:19]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86618692HCID 86618692, compound

Product 1

HCID 86618693HCID 86618693, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl (2S)-2-({[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]oxy}methyl)piperidine-1-carboxylate (729 mg, 1.67 mmol) was dissolved in THF (10 ml) and tetrabutylammonium fluoride (1.0 M in THF, 2.5 ml, 2.5 mmol) added. The reaction stirred at rt. for 1 h and the solvent removed in vacuo. Purification by silica gel flash chromatography using a Biotage 25+M column with EtOAc/heptane 1:1 yielded the title compound as a colorless oil. Yield: 520 mg (97%). 1H NMR (400 MHz, CDCl3) δ 7.52 (t, 1H, J=7.8 Hz), 6.76 (d, 1H, J=7.3 Hz), 6.59 (d, 1H, J=8.2 Hz), 4.68-4.61 (m, 3H), 4.50 (dd, 1H, J=10.6 Hz, J=7.2 Hz), 4.32 (dd, 1H, J=10.2 Hz, J=7.7 Hz), 4.01 (d, 1H, J=11.6 Hz), 3.59 (bs, 1H), 2.86 (dt, 1H, J=13.1 Hz, J=2.3 Hz), 1.81 (d, 1H, J=11.9 Hz), 1.67-1.49 (m, 5H), 1.38 (s, 9H).

Workup

  1. customthe solvent removed in vacuo
  2. customPurification by silica gel flash chromatography

Sources & evidence

ORD record
ord-6241f1433d5c4f6dbd93ea6c7bd605ea
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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