[7-(3,6-dihydro-2H-pyran-4-yl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester → [4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-carbamic acid methyl ester

HRID 1611938Notes

Reaction equation

HRID 1611938 reaction equation
[CH3:1][O:2][C:3](=[O:22])[NH:4][C:5]1[O:6][C:7]2[C:13]([C:14]3[CH2:15][CH2:16][O:17][CH2:18][CH:19]=3)=[CH:12][CH:11]=[C:10]([O:20][CH3:21])[C:8]=2[N:9]=1>CO.ClCCl.[Pd]>[CH3:1][O:2][C:3](=[O:22])[NH:4][C:5]1[O:6][C:7]2[C:13]([CH:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[CH:12][CH:11]=[C:10]([O:20][CH3:21])[C:8]=2[N:9]=1

Participants

5

Reactant 1

HCID 23593641[7-(3,6-dihydro-2H-pyran-4-yl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester

Product 1

HCID 23593640[4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-carbamic acid methyl esterYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 130 g (4.27 mmol) [7-(3,6-dihydro-2H-pyran-4-yl)-4-methoxy-benzooxazol-2-yl]-carbamic acid methyl ester in 250 ml methanol and 250 ml dichoromethane was added 1.00 g of 10% palladium on charcoal, and the mixture was then stirred for 10 h at room temperature under an atmosphere of hydrogen. The mixture was then filtered, washing with dichloromethane/methanol (1/1), and the filtrate concentrated in vacuo to afford 1.30 g (100%) [4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-carbamic acid methyl ester as an off-white solid. ES-MS m/e (%): 307 (M+H+, 100).

Workup

  1. filtrationThe mixture was then filtered
  2. washwashing with dichloromethane/methanol (1/1)
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-f3b60974e8da4fe58932e06b4127acf4
Source dataset
uspto-grants-2006_01
Patent number
US06992083B2

Reaction notes

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