Thiophene → HCID 18694173, compound

HRID 1870995Notes

Reaction equation

HRID 1870995 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:20]([O-])=O)[C:5]2[O:10][CH:9]([CH2:11][O:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[CH2:8][CH2:7][C:6]=2[CH:19]=1.S1C=CC=C1>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH2:20])[C:5]2[O:10][CH:9]([CH2:11][O:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[CH2:8][CH2:7][C:6]=2[CH:19]=1

Participants

5

Reactant 2

HCID 8030ThiopheneHCID 18694197HCID 18694197, compound

Product 1

HCID 18694173HCID 18694173, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of intermediate 15-b (0.47 mol) in methanol (600 ml) was hydrogenated with palladium on activated carbon, palladium content 10% (5 g) as a catalyst in the presence of a 4% thiophene solution (3 ml). After uptake of H2 (3 equiv), the catalyst was filtered off and the filtrate was evaporated, yielding 130 g (98.3%) of (±)-6-fluoro-3,4-dihydro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]-2H-1-benzopyran-8-amine (interm. 16-b).

Workup

  1. filtrationAfter uptake of H2 (3 equiv), the catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-a1b508bf851d4c44b59b591b3ad5e87a
Source dataset
uspto-grants-2000_08
Patent number
US06100268

Reaction notes

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