Tetrabutylammonium Fluoride → HCID 59737024, compound

HRID 1660729Notes

Reaction equation

HRID 1660729 reaction equation
S(O[CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:18]1[CH:19]=[C:20]([O:24][CH2:25][C@@H:26]2[CH2:29][CH2:28][N:27]2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:21]=[N:22][CH:23]=1)(C1C=CC(C)=CC=1)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.[F-:54]>C1COCC1>[F:54][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:18]1[CH:19]=[C:20]([O:24][CH2:25][C@@H:26]2[CH2:29][CH2:28][N:27]2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:21]=[N:22][CH:23]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59737028HCID 59737028, compound

Product 1

HCID 59737024HCID 59737024, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(6-tosyloxy-1-hexynyl)-3-(1-tert-butoxycarbonyl -2(S)-azetidinylmethoxy)pyridine (35 mg, 68 μmol) in 1 mL of 1.0 M solution of TBAF in THF was stirred at room temperature for 10 h. The reaction mixture concentrated. The residue was purified by chromatography with hexane-EtOAc (3:1) to give a viscous oil (25 mg, 100%), [α]D−40.6 (c 1.4, CHCl3). 1H NMR (CDCl3) δ 8.24 (s, 2H), 7.24 (m, 1H), 4.52 (dt, 2H, J=47.3, 6.0 Hz), 4.56-4.47 (m, 1H), 4.38-4.26 (m, 1H), 4.12 (dd, 1H, J=10.2, 2.7 Hz), 3.89 (t, 2H, J=7.8 Hz), 2.50 (t, 2H, J=6.9 Hz), 2.42-2.21 (m, 2H), 2.04-1.69 (m, 4H), 1.42 (s, 9H); 13C NMR (CDCl3) δ 156.13, 154.40, 144.85, 137.26, 123.22, 121.05, 92.94, 83.54 (d, J=164.7 Hz), 79.74, 77.69, 68.69, 60.00, 53.62, 47.09, 29.53 (d, J=20.2 Hz), 28.38, 24.31 (d, J=5.0 Hz), 19.03; 19F NMR (CDCl3, CFCl3) δ 135.4 (tt, J=47.3, 24.4 Hz).

Workup

  1. concentrationThe reaction mixture concentrated
  2. customThe residue was purified by chromatography with hexane-EtOAc (3:1)

Sources & evidence

ORD record
ord-16e21cf486d946888436876d30445974
Source dataset
uspto-grants-2011_10
Patent number
US08030300B2

Reaction notes

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