HCID 86703317, compound → HCID 69096715, compound

HRID 2410002Notes

Reaction equation

HRID 2410002 reaction equation
O[CH:2]([C:4]1[CH:5]=[CH:6][C:7]([CH3:18])=[C:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:9]=1)[CH3:3]>C(OCC)(=O)C.[Pd]>[CH2:2]([C:4]1[CH:5]=[CH:6][C:7]([CH3:18])=[C:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH:9]=1)[CH3:3]

Participants

4

Reactant 1

HCID 86703317HCID 86703317, compound

Product 1

HCID 69096715HCID 69096715, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl [5-(1-hydroxyethyl)-2-methylphenyl]carbamate (2.39 g) in ethyl acetate (47.5 mL) was added 10% palladium on carbon (56.5% water included, 1.10 g), and the mixture was stirred at room temperature for 6 hours under a hydrogen atmosphere. The reaction mixture was filtered through celite (registered trademark) pad. The filtrate was concentrated under reduced pressure to obtain the title compound (2.23 g). 1H-NMR (DMSO-d6) δ ppm: 1.14 (3H, t, J=7.5 Hz), 1.45 (9H, s), 2.13 (3H, s), 2.53 (2H, q, J=7.5 Hz), 6.82-6.90 (1H, m), 7.05 (1H, d, J=7.8 Hz), 7.11-7.18 (1H, m), 8.42 (1H, s).

Workup

  1. filtrationThe reaction mixture was filtered through celite (registered trademark) pad
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-38ad32b64a954c549bee534654961233
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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