4-Benzyloxy-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide → 4-hydroxy-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

HRID 1643676Notes

Reaction equation

HRID 1643676 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([C:10]2[CH:21]=[C:20]([O:22]CC3C=CC=CC=3)[C:13]3[CH2:14][CH:15]([CH2:17][O:18][CH3:19])[O:16][C:12]=3[CH:11]=2)=[O:9])=[N:3]1>CCOC(C)=O.[Pd]>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([C:10]2[CH:21]=[C:20]([OH:22])[C:13]3[CH2:14][CH:15]([CH2:17][O:18][CH3:19])[O:16][C:12]=3[CH:11]=2)=[O:9])=[N:3]1

Participants

4

Reactant 1

HCID 595600244-Benzyloxy-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

Product 1

HCID 595601864-hydroxy-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amideYield 102.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Pd on Carbon (100 mg) was added to a solution of 4-benzyloxy-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide (204c) (640 mg, 1.63 mmol) in EtOAc (15 mL). The reaction mixture was stirred under H2 balloon overnight. The mixture was filtered through Celite, washed with EtOAc and concentrated to give a white solid (508 mg, 100% yield). 1H NMR (400 MHz, CDCl3) δ 8.77 (s, 1 H) 7.96 (s, 1 H) 7.28 (d, J=2.27 Hz, 1 H) 6.98 (s, 1 H) 6.82 (s, 1 H) 6.78 (d, J=2.27 Hz, 1 H) 4.98-5.07 (m, 1 H) 3.76 (s, 3 H) 3.56-3.65 (m, 2 H) 3.44 (s, 3 H) 3.25 (dd, J=15.92, 9.60 Hz, 1 H) 2.97 (dd, J=16.04, 7.20 Hz, 1 H); LCMS for C15H17N3O4 m/z 304.00 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with EtOAc
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cd8cf730c18049c49db5c513a6c9161a
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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