(4-Hydroxy-2-(pyridin-3-yl)-1-oxa-9-azaspiro[5.5]undec-2-en-9-yl)(4-isopropoxy-3-methylphenyl)methanone → 4-Isopropoxy-3-methylbenzaldehyde

HRID 1478439Notes

Reaction equation

HRID 1478439 reaction equation
OC1C=C(C2C=NC=CC=2)OC2(CCN([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])CC2)C1>C(O)C.[Pd]>[CH:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([CH:10]=[O:11])=[CH:13][C:14]=1[CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 1

HCID 89704500(4-Hydroxy-2-(pyridin-3-yl)-1-oxa-9-azaspiro[5.5]undec-2-en-9-yl)(4-isopropoxy-3-methylphenyl)methanone

Product 1

HCID 509982434-Isopropoxy-3-methylbenzaldehydeYield 102.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

[8-hydroxy-10-(3-pyridyl)-11-oxa-3-azaspiro[5.5]undec-9-en-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (1.20 g, 2.84 mmol) was dissolved in ethanol. Under nitrogen, palladium (90.7 mg, 0.09 mmol) (10 wt % on carbon, wet) was added. The reaction system was flushed with hydrogen gas, and the mixture was stirred under a balloon of hydrogen gas overnight. The reaction mixture was filtered through a pad of celite. The concentrated filtrate was purified by column chromatography (70-100% ethyl acetate/hexane) to provide cis-8-hydroxy-10-(3-pyridyl)-11-oxa-3-azaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (520 mg) as a white foaming solid. 1H NMR (400 MHz, CDCl3) δ 8.65 (s, 1H), 8.57 (d, J=4.2 Hz, 1H), 7.80 (d, J=7.5 Hz, 1H), 7.37 (s, 1H), 7.19 (d, J=8.5 Hz, 2H), 6.80 (d, J=8.1 Hz, 1H), 4.65 (br s, 1H), 4.55 (dt, J=12.1, 6.0 Hz, 1H), 4.40 (br s, 1H), 4.17 (br s, 1H), 3.75-3.01 (m, 3H), 2.27-2.12 (m, 2H), 2.19 (s, 3H), 2.13-1.93 (m, 2H), 1.84-1.39 (m, 4H), 1.34 (d, J=6.0 Hz, 6H). ESI-MS m/z calc. 424.24, found 425.4 (M+1)+; Retention time: 1.13 minutes (3 min run).

Workup

  1. customThe reaction system was flushed with hydrogen gas
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. customThe concentrated filtrate was purified by column chromatography (70-100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f7b3e98c5f994bf6b059b2cb3e8d4dd0
Source dataset
uspto-grants-2016_08
Patent number
US09403839B2

Reaction notes

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