HCID 117817972, compound → HCID 117818017, compound

HRID 1772406Notes

Reaction equation

HRID 1772406 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][C:10](=[CH:17][C:18]1([CH3:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:11]2=[O:16]>[Ni].O.C(O)C>[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH:10]([CH2:17][C:18]1([CH3:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[C:11]2=[O:16]

Participants

5

Reactant 1

HCID 117817972HCID 117817972, compound

Product 1

HCID 117818017HCID 117818017, compoundYield 88.2%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of Raney nickel (a slurry in water, 4.4 g), compound 20 (4.4 g, 11.21 mmol, 1 equiv) in ethanol (450 mL) was hydrogenated @ 50 psi at room temperature overnight. The mixture was filtered through Celite and the filter cake was washed with ethanol (200 mL). The filtrate was concentrated under reduced pressure to give crude compound 21 (3.9 g, 88% yield) as a pale-yellow oil. This material was used subsequently.

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationThe mixture was filtered through Celite
  4. washthe filter cake was washed with ethanol (200 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-15ff89bff8cb4da38d81bf7777e5c898
Source dataset
uspto-grants-2016_02
Patent number
US09249239B2

Reaction notes

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