Triethylene Glycol → 26-Aminocholesterol

HRID 327775Notes

Reaction equation

HRID 327775 reaction equation
O=[C:2]1[CH2:37][C@@H:36]2[C@:23]([CH3:40])([CH2:24][CH2:25][C@H:26]3[C@H:35]2[CH2:34][CH:33]=[C:32]2[C@:27]3([CH3:39])[CH2:28][CH2:29][C@H:30]([OH:38])[CH2:31]2)[C@H:3]1[C@H:4]([CH3:22])[CH2:5][CH2:6][CH2:7][C@@H:8]([CH3:21])[CH2:9][N:10]1C(=O)C2=CC=CC=C2C1=O.O.NN.[OH-].[K+].C(O)COCCOCCO>O>[NH2:10][CH2:9][C@@H:8]([CH2:7][CH2:6][CH2:5][C@H:4]([C@@H:3]1[C@:23]2([CH3:40])[C@H:36]([C@H:35]3[C@H:26]([CH2:25][CH2:24]2)[C@:27]2([CH3:39])[C:32]([CH2:31][C@H:30]([CH2:29][CH2:28]2)[OH:38])=[CH:33][CH2:34]3)[CH2:37][CH2:2]1)[CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 8172Triethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 9832896(25R)-16-oxo-26-phthalimidocholesterol

Product 1

HCID 12633026-AminocholesterolYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (25R)-16-oxo-26-phthalimidocholesterol (5) (0.70 g, 1.32 mmoles), hydrazine monohydrate (5 ml, 102.8 mmoles), potassium hydroxide (2.85 g, 50.8 mmoles) and triethylene glycol (20 ml) was heated to 150° C. for 30 minutes, then heated to 200° C. over 2 hours during which time water vapor distilled out of the mixture. The reaction mixture was maintained at this temperature for about 16 hours, under nitrogen, until the reaction was complete as determined by thin layer chromatography. Thereafter, the reaction mixture was cooled, poured into water, and extracted with chloroform. The extract was washed with water, dried over sodium sulfate, and evaporated under reduced pressure. Chromatography of the residue on silica gel eluted with CHCl3 gave 0.34 g (66%) of (25R)-26-aminocholesterol. The product was recrystallized from methylene chloride-ether and was found to have a melting point of 150°-152° C.

Workup

  1. distillationvapor distilled out of the mixture
  2. temperatureThe reaction mixture was maintained at this temperature for about 16 hours, under nitrogen, until the reaction
  3. temperatureThereafter, the reaction mixture was cooled
  4. additionpoured into water
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated under reduced pressure
  9. washChromatography of the residue on silica gel eluted with CHCl3

Sources & evidence

ORD record
ord-41677efc9a4f47708f28cc5fd24acaa9
Source dataset
uspto-grants-1993_12
Patent number
US05274088

Reaction notes

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