[2-(4-Acetylamino-phenyl)-1,3-dihydroxy-indan-2-yl]-acetic acid ethyl ester → [2-(4-Acetylamino-phenyl)-indan-2-yl]-acetic Acid Ethyl Ester

HRID 1375080Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:26])[CH3:25])=[CH:19][CH:18]=2)[CH:14](O)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]1O)[CH3:2]>C(O)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1([C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:26])[CH3:25])=[CH:21][CH:22]=2)[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14]1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A stirred solution of [2-(4-acetylamino-phenyl)-1,3-dihydroxy-indan-2-yl]-acetic acid ethyl ester (0.38 g, Reference Example 12) in acetic acid (20 mL), under nitrogen, was treated with palladium black (20 mg), then the flask was evacuated and then hydrogen was introduced into the flask via a balloon. After stirring at 50° C. for 2 days the reaction mixture was filtered through Hi-flow supercel. The filtrate was concentrated then diluted with ethyl acetate (100 mL). This solution was washed with saturated sodium hydrogen carbonate solution (100 mL), then with water (100 mL), then dried over magnesium sulfate and then evaporated to give the title compound (0.296 g) as an amber coloured gum.

Workup

customthe flask was evacuated
additionhydrogen was introduced into the flask via a balloon
filtrationwas filtered through Hi-flow supercel
concentrationThe filtrate was concentrated
additionthen diluted with ethyl acetate (100 mL)
washThis solution was washed with saturated sodium hydrogen carbonate solution (100 mL)
dry with materialwith water (100 mL), then dried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-5cf2621d0b174eabad1f770dd5f890fd
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07166616B2

Reaction notes

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