HCID 86694602, compound → HCID 86694604, compound

HRID 63313Notes

Reaction equation

HRID 63313 reaction equation
[CH:1]1(/[CH:7]=[CH:8]/[C:9]2[O:13][C:12]([CH:14]([OH:24])[CH2:15][CH2:16][NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd]>[CH:1]1([CH2:7][CH2:8][CH:9]2[O:13][CH:12]([CH:14]([OH:24])[CH2:15][CH2:16][NH:17][C:18](=[O:23])[C:19]([F:21])([F:22])[F:20])[CH2:11][CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 86694602HCID 86694602, compound

Product 1

HCID 86694604HCID 86694604, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of (E)-N-(3-(5-(2-cyclohexylvinyl)furan-2-yl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide (0.11 g, 0.319 mmol) and Pd/C (10% wt, 0.037 g) in EtOAc (10 mL) was degassed by alternating vacuum/H2 three times and then stirred under H2 atmosphere at room temperature for 40 hrs, filtered through Celite and concentrated under reduced pressure to give N-(3-(5-(2-cyclohexylethyl)tetrahydrofuran-2-yl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide which was used directly in the next step without additional purification.

Workup

  1. custom0.037 g) in EtOAc (10 mL) was degassed
  2. filtrationfiltered through Celite
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6985121c9b294f878ffee1a6117173f4
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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