HCID 12230414, compound → HCID 19935718, compound

HRID 1438744Notes

Reaction equation

HRID 1438744 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]1[C:18]([CH3:26])([CH2:22][C:23]([OH:25])=[O:24])[O:19][CH2:20][CH2:21][C:12]2=1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]1[C:18]([CH3:26])([CH2:22][C:23]([OH:25])=[O:24])[O:19][CH2:20][CH2:21][C:12]2=1

Participants

5

Reactant 2

HCID 12230414HCID 12230414, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19935718HCID 19935718, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-benzyloxy-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid (5.3 g., 0.015 mole), prepared as described in Example 25, in 250 ml. of anhydrous ethanol, and 1.1 g. of 10% palladium on carbon is stirred at room temperature under a hydrogen atmosphere until no more hydrogen is being taken up by the reaction mixture. The catalyst is removed by filtration through diatomaceous earth (Celite) and the filtrate concentrated. The residue is recrystallized from ethanol-benzene to afford the title compound, m.p. 170°- 171° C.

Workup

  1. customprepared
  2. customThe catalyst is removed by filtration through diatomaceous earth (Celite)
  3. concentrationthe filtrate concentrated
  4. customThe residue is recrystallized from ethanol-benzene

Sources & evidence

ORD record
ord-c8fac39fc1474c9e9bb8fa32458413c9
Source dataset
uspto-grants-1977_11
Patent number
US04056537

Reaction notes

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