HCID 20346231, compound → HCID 20346206, compound

HRID 1701684Notes

Reaction equation

HRID 1701684 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.

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

Sources & evidence

ORD record
ord-9b498c67b5254e19bcb678030dfe1a85
Source dataset
uspto-grants-1980_03
Patent number
US04195025

Reaction notes

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