Diethyl Ether → HCID 86698320, compound

HRID 1050293Notes

Reaction equation

HRID 1050293 reaction equation
[N:1]([C@H:4]1[CH2:28][C@@:27]2([CH3:29])[CH:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:30])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:6][CH:5]1[OH:31])=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC>O>[NH2:1][C@H:4]1[CH2:28][C@@:27]2([CH3:29])[CH:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:30])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:6][CH:5]1[OH:31]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 86698321HCID 86698321, compound

Product 1

HCID 86698320HCID 86698320, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4 g 2β-azido-cholestane-3-ol and 0.2 g lithium aluminium hydride are stirred in 50 ml abs. ether for one day at room temperature. After careful decomposition with water and repeated ether extraction, the combined ethereal solutions are washed with water, dried over sodium sulfate and the solvent is reduced to 50 ml. Upon introduction of hydrogen chloride, the corresponding hydrochloride crystallizes out in the form of colorless needles which, after recrystallization from acidified methanol, melt at 254-256° C.

Workup

  1. extractionether extraction
  2. washthe combined ethereal solutions are washed with water
  3. dry with materialdried over sodium sulfate
  4. customUpon introduction of hydrogen chloride, the corresponding hydrochloride crystallizes out in the form of colorless needles which
  5. customafter recrystallization
  6. custommelt at 254-256° C.

Sources & evidence

ORD record
ord-d6e55441f86b4acc84f7b1588ed6eb5e
Source dataset
uspto-grants-2016_07
Patent number
US09382288B2

Reaction notes

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