(6-benzyloxy-1-methyl-1H-indol-3-yl)-oxo-acetic acid methyl ester → [6-hydroxy-1-methyl-1H-indole-3-yl]acetic acid methyl ester

HRID 250271Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:24])[C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15]CC3C=CC=CC=3)=[CH:12][CH:13]=2)[N:8]([CH3:23])[CH:7]=1)=O.O.[PH2]([O-])=O.[Na+]>O1CCOCC1.O.[Pd]>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[N:8]([CH3:23])[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (6-benzyloxy-1-methyl-1H-indol-3-yl)-oxo-acetic acid methyl ester (0.68 g, 2.10 mmol) in 1,4-dioxane (12 mL) is added a slurry of Pd/C (10%, 0.25 g). The flask is evacuated and re-filled with N2 three times. The mixture is heated to 100° C. and a solution of sodium hypophosphite, hydrate (5.0 g, 47 mmol) in water (5 mL) is added dropwise. The mixture is stirred at 100° C. for 16 hours and cooled to room temperature. The mixture is filtered through a pad of diatomaceous earth and the filtrate is concentrated under reduced pressure. The residue is purified via silica gel chromatography eluting with 25-50% EtOAc/Hexanes to provide the title compound (0.24 g, 52%). ES/MS m/e 220.0 (M+1), 218.0 (M−1).

Workup

customThe flask is evacuated
additionre-filled with N2 three times
temperaturecooled to room temperature
filtrationThe mixture is filtered through a pad of diatomaceous earth
concentrationthe filtrate is concentrated under reduced pressure
customThe residue is purified via silica gel chromatography
washeluting with 25-50% EtOAc/Hexanes

Sources & evidence

ORD record: ord-f654e00de34340f8991fccf303f34c0b
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863302B2

Reaction notes

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