Réaction #92532

ord-fb2a838865f14a8f93afdfdfeca7d614

Équation de réaction

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](N)CC[C@]4(C)[C@H]3CC[C@]12C
3α-Aminocholest-5-ene
O=C(O)CC(O)(CC(=O)O)C(=O)O
Citric acid
O=C(O)CC(O)(CC(=O)O)C(=O)O
citric acid
→
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](N)CC[C@]4(C)[C@H]3CC[C@]12C.O=C(O)CC(O)(CC(=O)O)C(=O)O
3α-aminocholest-5-ene citrate
Rendement 63.0%

Réactifs

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](N)CC[C@]4(C)[C@H]3CC[C@]12C
3α-Aminocholest-5-ene
O=C(O)CC(O)(CC(=O)O)C(=O)O
Citric acid
—
cholesterol amine
O=C(O)CC(O)(CC(=O)O)C(=O)O
citric acid

Réactifs

Aucun

Solvants

C1CCOC1
tetrahydrofuran
C1CCOC1
tetrahydrofuran

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autre(approximately 15 minutes)
  2. 2
    Filtrationfiltered
  3. 3
    LavageThe resulting white solid was washed with tetrahydrofuran
  4. 4
    Autrecollected
  5. 5
    Autredried under high vacuum for 12 hours

Mode opératoire

3α-Aminocholest-5-ene (0.82 mmol, 300 mg) was dissolved in 1.64 ml of tetrahydrofuran. Citric acid (0.82 mmol, 158 mg) was dissolved in 0.82 ml of tetrahydrofuran. The solution of citric acid was added dropwise to the solution of cholesterol amine. The mixture was stirred until the solution became very cloudy (approximately 15 minutes). The solution was vacuum filtered. The resulting white solid was washed with tetrahydrofuran, collected, and dried under high vacuum for 12 hours to produce 298 mg of the 3α-aminocholest-5-ene citrate in 63% yield. mp: 172-174° C.; IR (thin film): 3469, 2954, 2247, 1714, 1591 cm−1; 1H NMR (300 MHz, CD3OD) δ: 5.53 (d, 1H, J=5.2 Hz), 3.55 (s, 1H), 2.84-2.70 (m, 4H), 2.80-2.70 (m, 1H), 2.19-1.0 (m, 28H), 1.07 (s, 3H), 0.95 (3H, J=6.5 Hz), 0.89 (d, 6H, J=6.6 Hz), 0.73 (s, 3H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09447139B2uspto-grants-2016_09