HCID 89705315, compound → HCID 89705514, compound

HRID 1478453Notes

Reaction equation

HRID 1478453 reaction equation
[CH2:1]([C:3]1[CH2:26][CH:25]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[O:24][C:5]2([CH2:10][CH2:9][N:8]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([CH3:23])[CH:14]=3)=[O:12])[CH2:7][CH2:6]2)[CH:4]=1)[CH3:2]>CCO.[Pd]>[CH2:1]([C@H:3]1[CH2:4][C:5]2([CH2:10][CH2:9][N:8]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([CH3:23])[CH:14]=3)=[O:12])[CH2:7][CH2:6]2)[O:24][C@@H:25]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH2:26]1)[CH3:2]

Participants

4

Reactant 1

HCID 89705315HCID 89705315, compound

Product 1

HCID 89705514HCID 89705514, compoundYield 18.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of [8-ethyl-10-(3-pyridyl)-11-oxa-3-azaspiro[5.5]undec-7-en-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (90 mg, 0.21 mmol) in EtOH (14 mL) was purged with nitrogen for 5 min and then treated with 10% palladium on carbon (220 mg, 0.21 mmol). The mixture was evacuated and put under a hydrogen atmosphere (balloon). The reaction mixture was stirred for 4 h at 25° C. The reaction mixture was evacuated and put under an inert atmosphere. The Pd-catalyst was removed via filtration and was washed with ethyl acetate. The filtrate was concentrated to dryness. The crude mixture was purified on silica gel utilizing a gradient of 50-100% ethyl acetate and hexanes to yield (cis-4-ethyl-2-(pyridin-3-yl)-1-oxa-9-azaspiro[5.5]undecan-9-yl)(4-isopropoxy-3-methylphenyl)methanone (17 mg) ESI-MS m/z calc. 436.27, found 437.5 (M+1)+; Retention time: 1.68 minutes (3 min run).

Workup

  1. customThe mixture was evacuated
  2. customThe reaction mixture was evacuated
  3. customThe Pd-catalyst was removed via filtration
  4. washwas washed with ethyl acetate
  5. concentrationThe filtrate was concentrated to dryness
  6. customThe crude mixture was purified on silica gel utilizing a gradient of 50-100% ethyl acetate and hexanes

Sources & evidence

ORD record
ord-b936b7e022854dbea0705c2a13c66e5d
Source dataset
uspto-grants-2016_08
Patent number
US09403839B2

Reaction notes

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