HCID 86742936, compound → HCID 86742937, compound

HRID 1722456Notes

Reaction equation

HRID 1722456 reaction equation
[CH2:1]([C:3]1([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[C:16]#[C:17][CH3:18])[CH3:2].[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO>[CH2:1]([C:3]1([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3/[CH:16]=[CH:17]\[CH3:18])[CH3:2]

Participants

5

Reactant 2

HCID 86742936HCID 86742936, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86742937HCID 86742937, compoundYield 44.7%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-ethyl-8-(1-propynyl)-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, methyl ester (155 mg, 0.5 mmol), Lindlar catalyst (15 mg), and methanol (10 mL) was charged with 1 atmosphere of hydrogen and allowed to stir at room temperature overnight. The catalyst was then removed by filtration through a celite plug, and the filtrate concentrated to give 170 mg of the crude product. This material was purified by flash chromatography (10% ethyl acetate/hexane, silica gel) to give the pure title compound as yellow oil (70 mg).

Workup

  1. customThe catalyst was then removed by filtration through a celite plug
  2. concentrationthe filtrate concentrated
  3. customto give 170 mg of the crude product
  4. customThis material was purified by flash chromatography (10% ethyl acetate/hexane, silica gel)

Sources & evidence

ORD record
ord-62cab3529e214883810d9f6909c10989
Source dataset
uspto-grants-1989_08
Patent number
US04855445

Reaction notes

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