Tetrabutylammonium Fluoride → HCID 67428569, compound

HRID 1660730Notes

Reaction equation

HRID 1660730 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[CH2:30][CH2:29][CH2:28][N:27]2[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:21]=[N:22][CH:23]=1)(C1C=CC(C)=CC=1)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.[F-:55]>C1COCC1>[F:55][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[CH2:30][CH2:29][CH2:28][N:27]2[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:21]=[N:22][CH:23]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86761422HCID 86761422, compound

Product 1

HCID 67428569HCID 67428569, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(6-tosyloxy-1-hexynyl)-3-(1-tert-butoxycarbonyl -2(S)-pyrrolidinylmethoxy)pyridine (195 mg, 0.37 mmol) and in 2 mL of 1.0 M solution of TBAF in THF was stirred at room temperature for 15 h. The reaction mixture concentrated. The residue was purified by chromatography with hexane-EtOAc (3:1) to give a viscous oil (135 mg, 97%), [α]D=−58 (c 0.44, CHCl3). 1H NMR (CDCl3) δ 8.21 (m, 2H), 7.23 (br s, 1H), 4.52 (dt, 2H, J=47.3, 6.0 Hz), 4.14 (br s, 2H), 4.05-3.75 (m, 1H), 3.50-3.25 (m, 2H), 2.49 (t, 2H, J=6.9 Hz), 2.08-1.70 (m, 8H), 1.48 (s, 9H); 13C NMR (CDCl3) δ 154.37, 144.82 and 144.57, 137.38 and 137.08, 123.03, 121.03, 83.56 (d, J=165.2 Hz), 79.53, 68.65 and 68.41, 55.99 and 55.62, 46.97 and 46.60, 29.67 and 29.41, 28.51, 28.03, 24.32 (d, J=4.5 Hz), 23.87, 22.82, 19.04; 19F NMR (CDCl3, CFCl3) δ 131.0 (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-43efe2323d704eaa96b861295eceaef8
Source dataset
uspto-grants-2011_10
Patent number
US08030300B2

Reaction notes

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