Tetrabutylammonium Fluoride → HCID 67135302, compound

HRID 1631047Notes

Reaction equation

HRID 1631047 reaction equation
[Cl:1][C:2]1[C:3]([N:29]2[CH2:33][C@H:32]([O:34][Si](C(C)(C)C)(C)C)[CH2:31][C@H:30]2[C:42]([O:44][CH3:45])=[O:43])=[N:4][CH:5]=[C:6]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:25])=[C:15]([CH2:26][O:27][CH3:28])[CH:14]=3)[O:10][N:9]=2)[CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(Cl)Cl.O>[Cl:1][C:2]1[C:3]([N:29]2[CH2:33][C@H:32]([OH:34])[CH2:31][C@H:30]2[C:42]([O:44][CH3:45])=[O:43])=[N:4][CH:5]=[C:6]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:25])=[C:15]([CH2:26][O:27][CH3:28])[CH:14]=3)[O:10][N:9]=2)[CH:7]=1

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86660286HCID 86660286, compound

Product 1

HCID 67135302HCID 67135302, compoundYield 88.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (2S,4R)-1-(3-chloro-5-(5-(2-(methoxymethyl)-2′-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)-4-(tert-butyldimethylsilyloxy)-pyrrolidine-2-carboxylate (0.118 g; 0.18 mmol) in THF (2 mL) was added a solution of tetrabutylammonium fluoride (1.0 M in THF; 0.36 mL; 0.36 mmol). The reaction mixture was stirred at ambient temperature for 18 hours. The mixture was diluted with DCM and water and poured through a hydrophobic frit. The solvent was evaporated in vacuo and the residue was purified by flash chromatography on silica, eluting with iso-hexane/EtOAc (100% iso-hexane to 50%/50% iso-hexane/EtOAc) to afford the title product (0.085 g; 88%). 1H NMR (CDCl3, 400 MHz) δ 8.81 (1H, d, J=2 Hz), 8.40 (1H, d, J=1.2 Hz), 8.26 (1H, d, J=1.6 Hz), 8.15-8.13 (1H, m), 7.34-7.24 (4H, m), 7.14-7.12 (1H, m), 5.01 (1H, t, J=8 Hz), 4.66 (1H, s), 4.34-4.30 (1H, m), 4.22-4.21 (2H, m), 4.02-3.99 (1H, m), 3.74 (3H, s), 3.33 (3H, s), 2.38 (1H, m), 2.21-2.14 (1H, m), 2.08 (3H, s), 1.76 (1H, d, J=3.6 Hz).

Workup

  1. additionpoured through a hydrophobic frit
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified by flash chromatography on silica
  4. washeluting with iso-hexane/EtOAc (100% iso-hexane to 50%/50% iso-hexane/EtOAc)

Sources & evidence

ORD record
ord-93c9988d65d34700bb9a02c631b69e89
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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