Methyl-3-(benzyloxy)-5-[(1-methyl-2-oxopyrrolidin-3-yl)oxy]benzoate → Methyl 3-hydroxy-5-(1-methyl-2-oxopyrrolidin-3-yloxy)benzoate

HRID 75967Notes

Reaction equation

HRID 75967 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([O:10][CH:11]2[CH2:15][CH2:14][N:13]([CH3:16])[C:12]2=[O:17])[CH:7]=[C:6]([O:18]CC2C=CC=CC=2)[CH:5]=1>C1COCC1.CO.[Pd]>[OH:18][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH:11]2[CH2:15][CH2:14][N:13]([CH3:16])[C:12]2=[O:17])[CH:7]=1)[C:3]([O:2][CH3:1])=[O:26]

Participants

5

Reactant 1

HCID 66972240Methyl-3-(benzyloxy)-5-[(1-methyl-2-oxopyrrolidin-3-yl)oxy]benzoate2×

Product 1

HCID 66971906Methyl 3-hydroxy-5-(1-methyl-2-oxopyrrolidin-3-yloxy)benzoateYield 71.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Methyl-3-(benzyloxy)-5-[(1-methyl-2-oxopyrrolidin-3-yl)oxy]benzoate (6.1 g) (Intermediate 6) was dissolved in THF: Methanol mixture (1:1), and 10% Pd/C (0.6 g) was added to this mixture. The reaction mixture was stirred under hydrogen atmosphere for 16 h. After 16 h, TLC showed absence of starting material and formation of polar spot when checked in 10% methanol: chloroform, the reaction mixture was filtered through celite on Buckner funnel. The filtrate was concentrated under vacuum to get the solid product (3.27 g). 1H NMR (CDCl3, 400 MHz) δ ppm: 1.89-1.92 (m, 1 H), 2.51-2.54 (m, 1 H), 2.77 (s, 3 H), 3.34-3.37 (m, 2 H), 3.80 (s, 3 H), 4.96 (t, J=7.2 Hz, 1 H), 6.66 (t, J=2 Hz, 1 H), 6.97 (t, J=1.6 Hz, 1 H), 7.01 (t, J=1.2 Hz, 1 H), 9.88 (s, 1H); ESI MS m/z (relative intensities): 266.2 (M+H)+ (100%); UPLC Purity: 99.00%, Ret. time: 2.67 min.

Workup

  1. waitAfter 16 h
  2. filtrationchloroform, the reaction mixture was filtered through celite on Buckner funnel
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-3e8bb1d958314ad9b19ff38ba2de0513
Source dataset
uspto-grants-2014_09
Patent number
US08835469B2

Reaction notes

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