Triacetoxyperiodinane → HCID 24948914, compound

HRID 877394Notes

Reaction equation

HRID 877394 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][N:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[N:19]=2)[OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[N:16]=[N:17][N:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[N:19]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58366210HCID 58366210, compound

Product 1

HCID 24948914HCID 24948914, compoundYield 115%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Phenyl-1-(2-(pyridin-2-yl)-2H-tetrazol-5-yl)-heptan-1-ol (2.7 mg, 0.007 mmol) was dissolved in CH2Cl2 (0.24 mL) and Dess-Martin periodinane (4.5 mg, 0.011 mmol) was added. The mixture was stirred at room temperature for 2 h before the reaction mixture was reduced to half volume and this mixture was directly loaded onto silica gel and purified by flash chromatography (SiO2, 0.5×4 cm, 10-30% EtOAc-hexanes) to afford 7-phenyl-1-(2-(pyridin-2-yl)-2H-tetrazol-5-yl)-heptan-1-one (15b, 2.7 mg, 99%) as a white solid: 1H NMR (CDCl3, 600 MHz) δ 8.74 (m, 1H), 8.23 (m, 1H), 8.05 (dt, 1H, J=1.6, 7.9 Hz), 7.57 (dd, 1H, J=4.8, 7.5 Hz), 7.27 (t, 2H, J=7.6 Hz), 7.17 (m, 3H), 3.26 (t, 2H, J=7.4 Hz), 2.61 (t, 2H, J=7.7 Hz), 1.83 (m, 2H), 1.64 (m, 2H), 1.43 (m, 4H); 13C NMR (CDCl3, 150 MHz) δ 191.5, 162.5, 149.9, 148.6, 142.8, 139.8, 128.5, 128.4, 126.0, 125.8, 115.9, 41.0, 36.0, 31.4, 29.1, 29.0, 23.5; HRMS-ESI-TOF m/z 336.1813 ([M+H]+, C19H21N5O requires 336.1819). Purity 99%.

Workup

  1. custompurified by flash chromatography (SiO2, 0.5×4 cm, 10-30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-233acb38011649f69efc7965afbe2c38
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

Loading…