Hydrochloric Acid → HCID 21144152, compound

HRID 266007Notes

Reaction equation

HRID 266007 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 21144152HCID 21144152, compoundYield 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 1N 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-be0ea7383fce4276880546699d10be67
Source dataset
uspto-grants-1997_07
Patent number
US05650096

Reaction notes

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