Triacetoxyperiodinane → HCID 89704569, compound

HRID 1478451Notes

Reaction equation

HRID 1478451 reaction equation
[OH:1][CH:2]1[CH2:25][CH:24]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[O:23][C:4]2([CH2:9][CH2:8][N:7]([C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH:19]([CH3:21])[CH3:20])=[C:14]([CH3:22])[CH:13]=3)=[O:11])[CH2:6][CH2:5]2)[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]([N:7]2[CH2:8][CH2:9][C:4]3([O:23][CH:24]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[CH2:25][C:2](=[O:1])[CH2:3]3)[CH2:5][CH2:6]2)=[O:11])=[CH:13][C:14]=1[CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 89705304HCID 89705304, compound

Product 1

HCID 89704569HCID 89704569, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [8-hydroxy-10-(3-pyridyl)-11-oxa-3-azaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (100 mg, 0.24 mmol) in dichloromethane (3.4 mL) was cooled to 0° C. and treated with Dess-Martin periodinane (100 mg, 0.24 mmol). The reaction mixture was stirred for two hours and was quenched by the addition of saturated aqueous sodium sulfite. The mixture was extracted with dichloromethane (3×25 mL), and the combined organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified on silica gel utilizing a gradient of 50-100% ethyl acetate in hexanes to yield 3-(4-isopropoxy-3-methyl-benzoyl)-10-(3-pyridyl)-11-oxa-3-azaspiro[5.5]undecan-8-one (84 mg) ESI-MS m/z calc. 422.22, found 423.3 (M+1)+; Retention time: 1.41 minutes (3 min run).

Workup

  1. customwas quenched by the addition of saturated aqueous sodium sulfite
  2. extractionThe mixture was extracted with dichloromethane (3×25 mL)
  3. dry with materialthe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified on silica gel utilizing a gradient of 50-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-24413ce9dc56426f80adfbd2c073d10e
Source dataset
uspto-grants-2016_08
Patent number
US09403839B2

Reaction notes

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