tert-Butyl 2-(7-Hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylidene)acetate → tert-butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

HRID 515658Notes

Reaction equation

HRID 515658 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][C:13](=[CH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1.[H][H]>C(OCC)(=O)C.[Pd]>[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH:13]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 86654868tert-Butyl 2-(7-Hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylidene)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 67249455tert-butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetateYield 56.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylidene)acetate (230 mg, 0.806 mmol) was dissolved in ethyl acetate (5 mL). Degussa wet (50 wt % water) 10% Pd/C (223 mg, 0.105 mmol) was added and the mixture was stirred in a hydrogenation reactor under 95 psi hydrogen for 3 h. The mixture was filtered through Celite®. The filtrate was concentrated and purified by silica gel flash chromatography to provide the title compound as a white solid (131 mg). LCMS m/z=288.3 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationThe filtrate was concentrated
  3. custompurified by silica gel flash chromatography

Sources & evidence

ORD record
ord-13e80a3b9bd0487b8a188d2904f96db7
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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