HCID 20346231, compound → HCID 20346206, compound

HRID 261869Notes

Reaction equation

HRID 261869 reaction equation
[OH:1][C:2]1[C:11]2[CH:10]3[CH2:12][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:14][CH2:15][CH:9]3[C:8]([CH3:21])([CH3:20])[O:7][C:6]=2[CH:5]=[C:4]([C:22]([CH3:30])([CH3:29])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:3]=1>[Pd].C(O)C>[OH:1][C:2]1[C:11]2[CH:10]3[CH2:12][CH:13]([NH:16][C:17](=[O:19])[CH3:18])[CH2:14][CH2:15][CH:9]3[C:8]([CH3:20])([CH3:21])[O:7][C:6]=2[CH:5]=[C:4]([C:22]([CH3:29])([CH3:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:3]=1

Participants

4

Reactant 1

HCID 20346231HCID 20346231, compound

Product 1

HCID 20346206HCID 20346206, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1.177 g. of dl-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-9-(acetamido)-6a,7,10,10a-tetrahydro-6H-dibenzo[b,d]pyran in 100 ml. of ten percent aqueous ethanol containing 0.5 g. of five percent palladium suspended on carbon was stirred at 50° C. for 12 hours under a hydrogen atmosphere at 50 psi. The reaction mixture then was cooled to room temperature and filtered. The filtrate was concentrated to dryness by evaporation under reduced pressure to provide 1.06 g. of dl-trans-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-9-(acetamido)-6a,7,8,9,10,10a-hexahydro-6H-dibenzo[b,d]pyran. Nuclear magnetic resonance spectroscopy demonstrated the product thus formed to be indentical to that prepared in Example 5.

Workup

  1. temperatureThe reaction mixture then was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to dryness by evaporation under reduced pressure
  4. customto provide 1.06 g
  5. customthus formed
  6. customthat prepared in Example 5

Sources & evidence

ORD record
ord-c1e7a840239248b095b79c1432c6a077
Source dataset
uspto-grants-1979_05
Patent number
US04152450

Reaction notes

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