HCID 86718520, compound → HCID 39239523, compound

HRID 929931Notes

Reaction equation

HRID 929931 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([OH:16])[C@@H:10]([N+:13]([O-])=O)[CH2:11][CH3:12])=[CH:5][CH:4]=1>C(O)C.[Pd]>[NH2:13][C@@H:10]([CH2:11][CH3:12])[C@H:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[OH:16]

Participants

4

Reactant 1

HCID 86718520HCID 86718520, compound

Product 1

HCID 39239523HCID 39239523, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (1S*,2S*)-1-(4-methoxyphenyl)-2-nitrobutan-1-ol (1.0 g, 4.44 mmol) in ethanol (20 mL) was purged with argon, and Pd/C (100 mg, 0.094 mmol) was added at room temperature. The sealed vessel was then purged and refilled with H2 and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was filtered over celite, washed with ethanol and concentrated. The residue was purified by column chromatography using CH2Cl2/MeOH/(NH4OH in H2O) from 100:0:0 to 80:20:1 to yield the title compound as a white solid (450 mg, 51.4%). LC-MS: [M+H] 196.1; Rt 0.44 min; (LCMS method 2).

Workup

  1. additionwas added at room temperature
  2. customThe sealed vessel was then purged
  3. additionrefilled with H2
  4. filtrationThe reaction mixture was filtered over celite
  5. washwashed with ethanol
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-dd0d366de7be443eafb40e5203ac5a35
Source dataset
uspto-grants-2016_03
Patent number
US09296733B2

Reaction notes

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