Ammonia → HCID 86743348, compound

HRID 1607081Notes

Reaction equation

HRID 1607081 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]([CH2:32][CH3:33])[C:10]([NH:12][C@H:13]1[CH2:27][C@H:26]2[C@@H:16]([CH2:17][C:18]3[C:28]4[C:21](=[CH:22][C:23]([CH:29]=[O:30])=[CH:24][C:25]2=4)[NH:20][CH:19]=3)[N:15]([CH3:31])[CH2:14]1)=[O:11])[CH3:8].Cl.C(O)(=O)C(C(C(O)=O)O)O.N>C1COCC1>[CH2:32]([N:9]([CH2:7][CH3:8])[C:10]([NH:12][C@H:13]1[CH2:27][C@H:26]2[C@@H:16]([CH2:17][C:18]3[C:28]4[C:21](=[CH:22][C:23]([CH2:29][OH:30])=[CH:24][C:25]2=4)[NH:20][CH:19]=3)[N:15]([CH3:31])[CH2:14]1)=[O:11])[CH3:33]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 8752,3-Dihydroxybutanedioic AcidHCID 13823182HCID 13823182, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 86743348HCID 86743348, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

80 mg of lithium aluminum hydride (2 mmol) is suspended in 5 ml of anhydrous, freshly distilled THF and, at room temperature, a solution of 350 mg of 1,1-diethyl-3-(13-formyl-6-methyl-8α-ergolinyl)urea (1 mmol), dissolved in 10 ml of anhydrous, freshly distilled THF, is added thereto. After one hour of stirring at room temperature, the mixture is combined under cooling with 5 ml of 1N hydrochloric acid, 5 ml of 2N tartaric acid solution is added, and the mixture is rendered alkaline with aqueous ammonia, extracted with ethyl acetate, the organic phase dried and evaporated. After chromatography on silica gel, the compound is crystallized from ethyl acetate.

Workup

  1. additionis added
  2. additionis added
  3. extractionextracted with ethyl acetate
  4. customthe organic phase dried
  5. customevaporated
  6. customAfter chromatography on silica gel, the compound is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-e1095a733f264504b867b3a594f1f342
Source dataset
uspto-grants-1989_09
Patent number
US04863929

Reaction notes

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