Water → 3alpha-Aminocholest-5-ene

HRID 64252

반응식

HRID 64252 반응식
[N:1]([C@@H:4]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:5]1)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[NH2:1][C@@H:4]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:5]1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 133796253alpha-Azidocholest-5-eneHCID 21226445Aluminium lithium hydride

생성물 1

HCID 133964113alpha-Aminocholest-5-ene수율 93%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
0 °C

실험 절차

3α-Azidocholest-5-ene (4.62 mmol, 1.9 g) was dissolved in 154 mL of anhydrous diethyl ether. Lithium aluminum hydride (46.2 mmol, 1.75 g) was then added in one portion. After 30 hours, the reaction mixture was cooled to 0° C. 1.75 mL of deionized water was then added dropwise. After stirring for five minutes, 1.75 mL of 15% aqueous NaOH was added dropwise. After stirring for another five minutes, 5.25 mL of deionized water was added dropwise. The reaction was then stirred until all the salts turned white. Immediately afterwards, the reaction was filtered, dried (Na2SO4), and concentrated to afford 3α-Aminocholest-5-ene (1.57 g, 93%) as a white solid. mp 104-106° C.; IR (thin film) 3367, 3343, 2931, 1557 cm−1; 1H NMR (300 MHz, CDCl3) d 5.37-5.34 (m, 1H), 3.15 (t, 1H, J=3.2 Hz), 2.61-2.54 (m, 1H), 2.04-1.74 (m, 6H), 1.63-1.03 (m, 21H), 1.00 (s, 3H), 0.91 (d, 3H, J=6.5 Hz), 0.86 (d, 6H, J=6.6 Hz), 0.67 (s, 3H).

후처리

  1. stirringAfter stirring for another five minutes
  2. stirringThe reaction was then stirred until all the salts
  3. filtrationImmediately afterwards, the reaction was filtered
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a6342ea9989042ea9f7a10c29324fad0
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447139B2

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