HCID 117818011, compound → HCID 117817964, compound

HRID 1772401Notes

Reaction equation

HRID 1772401 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][C:18](=[CH:25][C:26]2([CH3:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:19]3=[O:24])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>[Ni].C(O)C>[C:11]([C:9]1[CH:8]=[C:7]([C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH:18]([CH2:25][C:26]2([CH3:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:19]3=[O:24])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1)([CH3:12])([CH3:13])[CH3:14]

Participants

4

Reactant 1

HCID 117818011HCID 117818011, compound

Product 1

HCID 117817964HCID 117817964, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of Raney nickel (slurry in water, 12.5 g), compound 12 (12.5 g, 29.16 mmol, 1 equiv) and ethanol (1000 mL) was hydrogenated @ 50 psi at room temperature for 4 hours. The mixture was filtered through Celite and the filter cake was washed with ethanol (500 mL). The filtrate was concentrated under reduced pressure to give crude compound 13 (10.0 g, 80% yield) as a pale-yellow oil. This material was used subsequently.

Workup

  1. customat room temperature
  2. customfor 4 hours
  3. filtrationThe mixture was filtered through Celite
  4. washthe filter cake was washed with ethanol (500 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-df0d5d77540846afacd180e887aab92b
Source dataset
uspto-grants-2016_02
Patent number
US09249239B2

Reaction notes

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