1,1-Diethyl-3[2-(1,3-dithiolan-2-yl)-1,6-dimethyl-8alpha-ergolinyl]urea → 1,1-Diethyl-3-(1,2,6-trimethyl8alpha-ergolinyl)urea

HRID 2352069Notes

Reaction equation

HRID 2352069 reaction equation
[CH2:1]([N:3]([CH2:30][CH3:31])[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)[N:14]([CH3:23])[C:13]=3[CH:24]2SCCS2)[N:9]([CH3:29])[CH2:8]1)=[O:5])[CH3:2]>CO>[CH2:30]([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)[N:14]([CH3:23])[C:13]=3[CH3:24])[N:9]([CH3:29])[CH2:8]1)=[O:5])[CH3:31]

Participants

3

Reactant 1

HCID 867434611,1-Diethyl-3[2-(1,3-dithiolan-2-yl)-1,6-dimethyl-8alpha-ergolinyl]urea

Product 1

HCID 867434621,1-Diethyl-3-(1,2,6-trimethyl8alpha-ergolinyl)ureaYield 27.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

7.5 ml of a Raney nickel suspension is washed four times with respectively 30 ml of methanol. Thereafter, 15 ml of methanol and then a solution of 690 mg (1.5 mmol) of 1,1-diethyl-3-[2-(1,3-dithiolan-2-yl)-1,6-dimethyl-8α-ergolinyl]urea in 15 ml of methanol are added thereto. The mixture is agitated for 3 hours at room temperature and then once more 7.5 ml of a Raney nickel suspension, previously washed as above four times with respectively 30 ml of methanol, is added thereto. After another 2 hours of agitation at room temperature, the catalyst is filtered off via a silica gel column and washed thoroughly with methanol. The filtrate is evaporated and the residue crystallized from methanol/ethyl acetate, thus obtaining 150 mg of 1,1-diethyl-3-(1,2,6-trimethyl8α-ergolinyl)urea (27% yield).

Workup

  1. wash7.5 ml of a Raney nickel suspension is washed four times with respectively 30 ml of methanol
  2. washonce more 7.5 ml of a Raney nickel suspension, previously washed as above four times with respectively 30 ml of methanol
  3. additionis added
  4. waitAfter another 2 hours of agitation at room temperature
  5. filtrationthe catalyst is filtered off via a silica gel column
  6. washwashed thoroughly with methanol
  7. customThe filtrate is evaporated
  8. customthe residue crystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-d01cb3a132194fa7860a3de6ed44213c
Source dataset
uspto-grants-1989_10
Patent number
US04874768

Reaction notes

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