Methanol → HCID 21156212, compound

HRID 1089872Notes

Reaction equation

HRID 1089872 reaction equation
[C:1]([N:5]1[C:19]2[C:20]3[C:7]([CH2:8][C@@H:9]4[C:14]([C:15]=3[CH:16]=[CH:17][CH:18]=2)=[CH:13][C@@H:12]([CH2:21][OH:22])[CH2:11][N:10]4[CH3:23])=[CH:6]1)([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)(O)O.[OH-:29].[NH4+].[CH3:31]O>O>[C:1]([N:5]1[C:19]2[C:20]3[C:7]([CH2:8][C@@H:9]4[C@@:14]([O:29][CH3:31])([C:15]=3[CH:16]=[CH:17][CH:18]=2)[CH2:13][C@@H:12]([CH2:21][OH:22])[CH2:11][N:10]4[CH3:23])=[CH:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 21156211HCID 21156211, compound

Product 1

HCID 21156212HCID 21156212, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6 g of 1-(t-butyl)-9,10-didehydro-6-methyl-8β-hydroxymethyl-ergoline, prepared as described in Example 1, in 500 ml of methanol and 5 ml of sulphuric acid was irradiated at 20° C. in a Pyrex flask with a Hanau PL 321 lamp for about 6 hours, until the absorption at 315 nm completely disappeared. The solution was diluted with iced water, made basic with ammonium hydroxide, evaporated to 100 ml and extracted with ethyl acetate. After evaporation of the solvent the residue was chromatographed in silica gel and on elution with 97:3 dichloromethane:methanol, 5 g of the title compound was isolated, m.p. 172 to 174° C. from acetone.

Workup

  1. customevaporated to 100 ml
  2. extractionextracted with ethyl acetate
  3. customAfter evaporation of the solvent the residue
  4. customwas chromatographed in silica gel and on elution with 97:3 dichloromethane

Sources & evidence

ORD record
ord-3734648caf0b49cea12e194d662dcbe6
Source dataset
uspto-grants-1992_01
Patent number
US05079364

Reaction notes

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