Triacetoxyperiodinane → HCID 68843550, compound

HRID 1784823Notes

Reaction equation

HRID 1784823 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:25]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)[OH:26])[CH:14]=[CH:15][C:16]=3[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOCC>[C:1]12([C:11]3[CH:12]=[C:13]([C:25]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[O:26])[CH:14]=[CH:15][C:16]=3[O:17][Si:18]([C:21]([CH3:23])([CH3:24])[CH3:22])([CH3:19])[CH3:20])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68846337HCID 68846337, compound

Product 1

HCID 68843550HCID 68843550, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

[3-Adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-pyridin-3-yl-methanol (55 mg, 0.112 mmol) was dissolved in methylene chloride. The Dess Martin periodane (0.104 g, 0.224 mmol) was then added to the reaction mixture. The reaction was complete within 10 min and was then diluted with ether. The organic layer was washed with Na2S2O4 (2×30 mL) followed by NaHCO3 (2×30 mL) followed by brine (1×30 mL) The organic layers were combined, dried with Na2SO4 and then evaporated to give [3-adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-pyridin-3-yl-methanone, which was deprotected without further purification. The deprotection was carried out as described for Example 62, except the reaction was complete after 10 min. The product was purified by chromatography to give 17 mg of 3-adamantan-1-yl-4-hydroxy-phenyl)-pyridin-3-yl-methanone as a white solid. 1H NMR (400 MHz, methanol-d4/CDCl3): δ 8.81 (d, J=2.1 Hz, 1H), 8.68 (dd, J=5.0, 1.7 Hz, 1H), 8.07 (td, J=8.0, 2.0 Hz, 1H), 7.70 (d, J=2.3 Hz, 1H), 7.52 (dd, J=5.0, 2.9 Hz, 1H), 7.48 (dd, J=8.6, 2.5 Hz, 1H), 6.80 (d, J=8.4 Hz, 1H), 2.10 (d, J=2.9 Hz, 6H), 2.02 (s, 3H), 1.74 (t, J=2.8 Hz, 6H)

Workup

  1. washThe organic layer was washed with Na2S2O4 (2×30 mL)
  2. dry with materialdried with Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-1503960581b64c7bacfc5d703c708315
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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