Imidazole → HCID 58366231, compound

HRID 877391Notes

Reaction equation

HRID 877391 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:15]2[N:16]=[N:17][NH:18][N:19]=2)[OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][C:21]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1>CN(C=O)C.CCOC(C)=O>[Si:24]([O:14][CH:13]([C:15]1[N:16]=[N:17][NH:18][N:19]=1)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:21]([CH3:23])([CH3:22])[CH3:20])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 58366268HCID 58366268, compound

Product 1

HCID 58366231HCID 58366231, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-phenyl-1-(2H-tetrazol-5-yl)-heptan-1-ol (36 mg, 0.14 mmol), TBSCl (63 mg, 0.42 mmol) and imidazole (28 mg, 0.42 mmol) in DMF (0.7 mL) was stirred at room temperature for 72 h before it was diluted with EtOAc, and washed with H2O and saturated aqueous NaCl. The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure to afford the crude material that was purified by flash chromatography (SiO2, 1.5×15 cm, 10% acetone-hexanes) to afford 5-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-2H-tetrazole (39 mg, 75%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 7.26 (dd, 2H, J=6.3, 8.4 Hz), 7.16 (m, 3H), 5.25 (t, 1H, J=5.8 Hz), 2.57 (t, 2H, J=7.7 Hz), 1.85 (m, 2H), 1.58 (m, 2H), 1.31 (m, 6H), 0.90 (s, 9H), 0.13 (s, 3H), 0.01 (s, 3H).

Workup

  1. washwashed with H2O and saturated aqueous NaCl
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent was removed under reduced pressure
  4. customto afford the crude material that
  5. customwas purified by flash chromatography (SiO2, 1.5×15 cm, 10% acetone-hexanes)

Sources & evidence

ORD record
ord-893ea4cb1561453dbc05712b840086a7
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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