HCID 86685420, compound → HCID 71060828, compound

HRID 1911011Notes

Reaction equation

HRID 1911011 reaction equation
C([N:8]1[C@:12]2([CH3:22])[C:13]3[CH:14]=[CH:15][C:16]([F:21])=[CH:17][C:18]=3[O:19][CH2:20][C@@H:11]2[CH2:10][O:9]1)C1C=CC=CC=1>[Pd].CO>[NH2:8][C@:12]1([CH3:22])[C:13]2[C:18](=[CH:17][C:16]([F:21])=[CH:15][CH:14]=2)[O:19][CH2:20][C@@H:11]1[CH2:10][OH:9]

Participants

4

Reactant 1

HCID 86685420HCID 86685420, compound

Product 1

HCID 71060828HCID 71060828, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (0.213 g, 0.200 mmol) was added under a nitrogen atmosphere to a solution of rel-(3aR,9bS)-1-benzyl-7-fluoro-9b-methyl-3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c]isoxazole from step F2 (1.2 g, 4.01 mmol), in MeOH (200 mL). The resulting flask was repeatedly flushed with hydrogen gas and vigorously stirred under an atmosphere of hydrogen (double balloon) for 24 h. The reaction mixture was purged with nitrogen, filtered through celite, and concentrated in vacuo. The filtrate was dissolved in MeOH and passed through a 0.45 um filter. The filtrate was concentrated in vacuo and dried under high vacuum to afford rel-((3S,4S)-4-amino-7-fluoro-4-methylchroman-3-yl)methanol (0.80 g, 3.8 mmol, 94% yield) as a viscous oil. The crude product was used for subsequent chemistry without purification or characterization.

Workup

  1. customThe resulting flask was repeatedly flushed with hydrogen gas
  2. customThe reaction mixture was purged with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated in vacuo
  5. dissolutionThe filtrate was dissolved in MeOH
  6. filtrationfilter
  7. concentrationThe filtrate was concentrated in vacuo
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-72a0438f2a1f4fb8834bd7359781f3e3
Source dataset
uspto-grants-2013_12
Patent number
US08604024B2

Reaction notes

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