Hydrochloric Acid → 3-Aminocholestane

HRID 1934307Notes

Reaction equation

HRID 1934307 reaction equation
C1(=O)[N:5]([CH:6]2[CH2:30][CH2:29][C@@:28]3([CH3:31])[CH:8]([CH2:9][CH2:10][C@@H:11]4[C@@H:27]3[CH2:26][CH2:25][C@@:24]3([CH3:32])[C@H:12]4[CH2:13][CH2:14][C@@H:15]3[C@H:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:7]2)C(=O)C2=CC=CC=C12.NN.Cl.[OH-].[Na+]>CO.C(OCC)C>[NH2:5][CH:6]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[CH:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:32])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C@H:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 14798Sodium HydroxideHCID 543667153-Phthalimidocholestane

Product 1

HCID 211441523-AminocholestaneYield 59.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The 3-phthalimidocholestane (5.40 g, 9.75 mmol) was dissolved in 60 mL of methanol and anhydrous hydrazine (3.1 ml, 99 mmol) was added. The reaction mixture was stirred and heated at reflux under a nitrogen atmosphere for 4 hr. This mixture was then cooled to room temperature, 3.1 mL of concentrated HCl was added and the resulting mixture was heated at reflux overnight. Upon cooling to ambient temperature, 100 ml of diethyl ether and 50 ml of 1 N NaOH were added (final pH of 10.1) and the layers were separated. The aqueous layer was extracted with 50 ml of diethyl ether and the combined organic fractions were filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (chloroform/methanol 90/10) to give 2.24 g of 3-aminocholestane in 59% yield.

Workup

  1. temperatureheated
  2. temperatureat reflux under a nitrogen atmosphere for 4 hr
  3. temperaturethe resulting mixture was heated
  4. temperatureat reflux overnight
  5. temperatureUpon cooling to ambient temperature
  6. customwere separated
  7. extractionThe aqueous layer was extracted with 50 ml of diethyl ether
  8. filtrationthe combined organic fractions were filtered
  9. concentrationThe filtrate was concentrated in vacuo
  10. customthe residue was purified by silica gel chromatography (chloroform/methanol 90/10)

Sources & evidence

ORD record
ord-5000ba0ed2be42bd836a9c89c4f78d26
Source dataset
uspto-grants-2002_05
Patent number
US06383814B1

Reaction notes

Loading…