HCID 67253499, compound → HCID 58292671, compound

HRID 1798155Notes

Reaction equation

HRID 1798155 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24]CC4C=CC=CC=4)[CH:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:32])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]

Participants

4

Reactant 1

HCID 67253499HCID 67253499, compound

Product 1

HCID 58292671HCID 58292671, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of [6-(3-benzyloxy-phenoxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (1.22 g, 2.82 mmol) and 10% Pd/C (1.0 g) in EtOH (20 mL) was hydrogenated at 40 psi for 30 minutes. The mixture was filtered through a pad of celite and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (hexane:EtOAc 50:50) to give [1-hydroxy-6-(3-hydroxy-phenoxy)-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.65 g, 68%). 1H NMR (400 MHz, DMSO): δ 7.13 (t, J=8.4 Hz, 1H), 7.06 (d, J=2.4 Hz, 1H), 6.95 (d, J=1.6 Hz, 1H), 6.50 (dd, J=1.6, 8.0 Hz, 1H), 6.38 (dd, J=1.6, 8.0 Hz, 1H), 6.32 (t, J=2.4 Hz, 1H), 5.48 (dd, J=2.4 Hz, 1H), 4.02 (q, J=7.2 Hz, 2H), 3.09 (dd, J=2.4 Hz, 1H), 2.29-2.23 (m, 1H), 2.26 (s, 3H), 1.12 (t, J=4.4 Hz, 3H). MS (ESI) m/z=341 [M−H]−.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel flash column chromatography (hexane:EtOAc 50:50)

Sources & evidence

ORD record
ord-959dabbb711b404b960e346ea375e058
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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