1,1-Diethyl-3-[2-(1,3-dithiolan-2-yl)-6-methyl-8alpha-ergolinyl]urea → 1,1-Diethyl-3-(2,6-dimethyl-8alpha-ergolinyl)urea
Reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[NH:14][C:13]=3[CH:23]2SCCS2)[N:9]([CH3:28])[CH2:8]1)=[O:5])[CH3:2]>CO.[Ni]>[CH2:29]([N:3]([CH2:1][CH3:2])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[NH:14][C:13]=3[CH3:23])[N:9]([CH3:28])[CH2:8]1)=[O:5])[CH3:30]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
7.5 ml of a Raney nickel suspension is washed four times with respectively 30 ml of methanol. Then 15 ml of methanol and thereafter a solution of 670 mg (1.5 mmol) of 1,1-diethyl-3-[2-(1,3-dithiolan-2-yl)-6-methyl-8α-ergolinyl]urea in 15 ml of methanol are added thereto. The mixture is agitated for 3 hours at room temperature and once again 7.5 ml of a Raney nickel suspension is added which has been washed, as above, previously four times with respectively 30 ml of methanol. After another 2 hours of agitation at room temperature, the catalyst is filtered off over a silica gel column and thoroughly washed with methanol. The filtrate is evaporated and the residue is crystallized from methanol/ethyl acetate, thus obtaining 170 mg of 1,1-diethyl-3-(2,6-dimethyl-8α-ergolinyl)urea (32% yield).
Workup
- wash7.5 ml of a Raney nickel suspension is washed four times with respectively 30 ml of methanol
- washhas been washed
- waitAfter another 2 hours of agitation at room temperature
- filtrationthe catalyst is filtered off over a silica gel column
- washthoroughly washed with methanol
- customThe filtrate is evaporated
- customthe residue is crystallized from methanol/ethyl acetate
Sources & evidence
- ORD record
- ord-1184ef5b1e1c41f79ea364d694c43630
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04731367
Reaction notes
Loading…