[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]1A 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.
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