Hydrochloric Acid → 3alpha-Aminocholest-5-ene hydrochloride

HRID 64253Notes

Reaction equation

HRID 64253 reaction equation
[NH2:1][C@@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:3]1.[ClH:29]>C(OCC)C>[ClH:29].[NH2:1][C@@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 133964113alpha-Aminocholest-5-ene

Product 1

HCID 674487523alpha-Aminocholest-5-ene hydrochlorideYield 46%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3α-Aminocholest-5-ene (1.61 mmol, 0.59 g) was dissolved in 2 mL of anhydrous diethyl ether. Hydrogen chloride (2.0 M in diethyl ether) (3.22 mmol, 1.61 mL) was then added. After 3 hours, a white precipitate formed. The reaction was then filtered and the solid was washed with diethyl ether to afford 3α-aminocholest-5-ene hydrochloride (0.31 g, 46%) as a white solid. mp 293-295° C.; IR (thin film) 2947 cm−1; 1H NMR (300 MHz, CDCl3) d 8.25 (s, 3H), 5.52 (d, 1H, J=4.3 Hz), 3.58 (s, 1H), 2.61 (d, 1H, J=14.6 Hz), 2.36 (d, 1H, J=15.0 Hz), 2.02-1.07 (m, 26H), 1.01 (s, 3H), 0.91 (d, 3H, J=6.3 Hz), 0.86 (d, 6H, J=6.6 Hz), 0.67 (s, 3H).

Workup

  1. customa white precipitate formed
  2. filtrationThe reaction was then filtered
  3. washthe solid was washed with diethyl ether

Sources & evidence

ORD record
ord-54c3bf9127c4469fbc9ab341f16ddfc6
Source dataset
uspto-grants-2016_09
Patent number
US09447139B2

Reaction notes

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