Ethanol → HCID 19013011, compound

HRID 1729540Notes

Reaction equation

HRID 1729540 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][N:6]([C:8]([OH:10])=[O:9])[C:5]2[CH:11]=[C:12]([O:19]CC3C=CC=CC=3)[C:13]3[NH:14][CH:15]=[C:16]([CH3:18])[C:17]=3[C:4]1=2.C(O)C>C1COCC1.[Pd]>[OH:1][CH2:2][CH:3]1[CH2:7][N:6]([C:8]([OH:10])=[O:9])[C:5]2[CH:11]=[C:12]([OH:19])[C:13]3[NH:14][CH:15]=[C:16]([CH3:18])[C:17]=3[C:4]1=2

Participants

5

Reactant 2

HCID 702EthanolHCID 19013010HCID 19013010, compound

Product 1

HCID 19013011HCID 19013011, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

242 mg (0.59 mM) of the product of step 2, 1,1-dimethylethyl ester of 1-(hydroxymethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid, is dissolved in distilled THF (2.4 ml) and absolute ethanol (25 ml). The compound is hydrogenalized over 10% palladium on carbon (192 mg) at 42 PSI for 50 minutes. The reaction is filtered through diatomaceous earth, washing with absolute ethanol. Evaporation yields compound 4, 1,1-dimethylethyl ester of 1-(hydroxymethyl)-1,6-dihydro-8-methyl-5-hydroxy-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid.

Workup

  1. filtrationThe reaction is filtered through diatomaceous earth
  2. washwashing with absolute ethanol
  3. customEvaporation

Sources & evidence

ORD record
ord-977b5d11c16f4f08aa812d4a9cd1f2a5
Source dataset
uspto-grants-1994_07
Patent number
US05332837

Reaction notes

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