Citric Acid → 3alpha-Aminocholest-5-ene citrate

HRID 64254Notes

Reaction equation

HRID 64254 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.[C:29]([OH:41])(=[O:40])[CH2:30][C:31]([CH2:36][C:37]([OH:39])=[O:38])([C:33]([OH:35])=[O:34])[OH:32]>O1CCCC1>[C:29]([OH:41])(=[O:40])[CH2:30][C:31]([CH2:36][C:37]([OH:39])=[O:38])([C:33]([OH:35])=[O:34])[OH:32].[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 311Citric Acid2×HCID 133964113alpha-Aminocholest-5-ene

Product 1

HCID 674507173alpha-Aminocholest-5-ene citrateYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  1. custom(approximately 15 minutes)
  2. filtrationfiltered
  3. washThe resulting white solid was washed with tetrahydrofuran
  4. customcollected
  5. customdried under high vacuum for 12 hours

Sources & evidence

ORD record
ord-fb2a838865f14a8f93afdfdfeca7d614
Source dataset
uspto-grants-2016_09
Patent number
US09447139B2

Reaction notes

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