1413-67-8 → HCID 22803977, compound

HRID 547957Notes

Reaction equation

HRID 547957 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH:18]=[C:17]2[C@@H:7]([CH2:8][C:9]3[C:19]4[C:12](=[CH:13][CH:14]=[CH:15][C:16]2=4)[NH:11][CH:10]=3)[N:5]([CH3:6])[CH2:4]1>[Pd].CN(C)C=O>[OH:1][CH2:2][C@@H:3]1[CH:18]=[C:17]2[C@@H:7]([CH2:8][CH:9]3[C:19]4[C:12](=[CH:13][CH:14]=[CH:15][C:16]2=4)[NH:11][CH2:10]3)[N:5]([CH3:6])[CH2:4]1

Participants

4

Reactant 1

HCID 149871413-67-8

Product 1

HCID 22803977HCID 22803977, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of Lysergol (1.5 g) and Palladium on carbon (5%, 50% wet, 75 mg) in N,N-dimethylformamide (15 mL) is hydrogenated at 50-60° C. and 40-50 psi until the theoretical volume of hydrogen has been absorbed. The reaction mixture is cooled, filtered and the insoluble material is washed with more N,N-dimethylformamide. The filtrate is evaporated to dryness and suspended with water. The resulting suspension is filtered, washed with more water. The solid is dried under vacuum to give 1.47 g of dihydrolysergol in 97% yield.

Workup

  1. customis hydrogenated at 50-60° C.
  2. custom40-50 psi until the theoretical volume of hydrogen has been absorbed
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. washthe insoluble material is washed with more N,N-dimethylformamide
  6. customThe filtrate is evaporated to dryness
  7. filtrationThe resulting suspension is filtered
  8. washwashed with more water
  9. customThe solid is dried under vacuum

Sources & evidence

ORD record
ord-7c7f1ab984f543b9a2886aea5399741c
Source dataset
uspto-grants-2011_05
Patent number
US07939665B2

Reaction notes

Loading…