Triacetoxyperiodinane → HCID 86599653, compound

HRID 2099831Notes

Reaction equation

HRID 2099831 reaction equation
[OH:1][CH2:2][CH:3]([CH2:12][C:13]1[CH:21]=[C:20]([CH3:22])[C:19]2[C:15](=[CH:16][N:17]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[N:18]=2)[CH:14]=1)[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([CH:3]([CH2:12][C:13]1[CH:21]=[C:20]([CH3:22])[C:19]2[C:15](=[CH:16][N:17]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[N:18]=2)[CH:14]=1)[CH2:4][C:5]([O:7][C:8]([CH3:10])([CH3:9])[CH3:11])=[O:6])=[O:1]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 69075929HCID 69075929, compound

Product 1

HCID 86599653HCID 86599653, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(hydroxymethyl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoate (0.5500 g, 1.27 mmol) in methylene chloride (25 mL) was added Dess-Martin reagent (0.6449 g, 1.52 mmol) at room temperature. The reaction was stirredo vernight before washing with 1 N sodium hydroxide (10 mL) and water (2×10 mL). The organic layer was dried, filtered and concentrated. The final product was obtained by flash chromatography using 0% to 50% ethyl acetate/hexane (0.2773 g, 51%) HPLC tR=2.02 min, 1H-NMR (400 MHz, CDCl3) δ 9.42 (1H, s), 7.94 (1H, s), 7.19 (1H, s), 6.82 (1H, s), 5.64 (2H, s), 3.57 (2H, t, J=8.40 Hz), 3.02 (2H, m), 2.58 (1H, m), 2.54 (3H, s), 2.49 (1H, m), 2.30 (1H, m), 1.33 (9H, s), 0.87 (2H, t, J=8.40 Hz), −0.01 (9H, s).

Workup

  1. washbefore washing with 1 N sodium hydroxide (10 mL) and water (2×10 mL)
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0ea6adb421434331857b8a14e05def9a
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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