HCID 118076067, compound → HCID 118076092, compound

HRID 1051559Notes

Reaction equation

HRID 1051559 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:6]=1[C:14]#[C:15][C@H:16]([OH:18])[CH3:17].[H][H]>[Pd].CO>[NH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH2:3][O:2][CH3:1])[C:6]=1[CH2:14][CH2:15][C@H:16]([OH:18])[CH3:17]

Participants

5

Reactant 2

HCID 118076067HCID 118076067, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118076092HCID 118076092, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 400-mL Parr bottle charged with (R)-4-(2-(methoxymethoxy)-6-nitrophenyl)but-3-yn-2-ol (2.9 g, 11.54 mmol), methanol (58 mL), and 10% palladium on carbon (50% water, 1.228 g, 0.577 mmol) was pressurized to 39 psig with hydrogen and then shaken. Hydrogen was quickly consumed, and within 15 min, the pressure had dropped to 0 psig. The bottle was re-pressurized to 39 psig and shaking was continued. The pressure dropped to ca. 20 psig over the next 15 min and stabilized. The bottle was re-pressurized to 34 psig and held there with continued shaking for 2 h. The mixture was flushed with nitrogen, and then filtered through a pad of Celite. The bottle and catalyst were rinsed with methanol, and the filtrate concentrated under reduced pressure. Toluene was added and the mixture was concentrated to afford (R)-4-(2-amino-6-(methoxymethoxy)phenyl)butan-2-ol (2.60 g, 100%) as a dark yellow syrup which was used without further purification. MS (ESI, pos. ion) m/z 248 [M+23]+.

Workup

  1. customHydrogen was quickly consumed
  2. additionthe pressure had dropped to 0 psig
  3. stirringshaking
  4. additionThe pressure dropped to ca. 20 psig over the next 15 min
  5. stirringwith continued shaking for 2 h
  6. customThe mixture was flushed with nitrogen
  7. filtrationfiltered through a pad of Celite
  8. washThe bottle and catalyst were rinsed with methanol
  9. concentrationthe filtrate concentrated under reduced pressure
  10. additionToluene was added
  11. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-590b8d25d5f246a4b5e15342bcdb422d
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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