Ammonia → HCID 70627247, compound

HRID 1834201Notes

Reaction equation

HRID 1834201 reaction equation
[F:1][C:2]([CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:27]2([CH3:28])[C@H:13]([C@H:14]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:17](=[CH:18][C@@H:19](O)[CH2:20][C@@H:21]2[OH:29])[CH:16]=[CH:15]3)[CH2:12][CH2:11]1)[CH3:9])([CH3:4])[CH3:3].N.[Li]>O1CCCC1>[F:1][C:2]([CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:27]2([CH3:28])[C@H:13]([C@H:14]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:17]([CH2:18][CH2:19][CH2:20][C@@H:21]2[OH:29])=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)[CH3:9])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 3028194LithiumHCID 70626539HCID 70626539, compound

Product 1

HCID 70627247HCID 70627247, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

25-Fluoro-4,6-cholestadiene-1α,3β-diol (0.005 mole) prepared according to 3B above is dissolved in 100 ml. of a 1:1 solvent mixture of tetrahydrofuran and liquid ammonia and stirred at reflux using a dry-ice condenser with 0.4 gm. of finely divided lithium for 1.0 hour. The liquid ammonia is allowed to evaporate and 10 ml. of water is added. The tetrahydrofuran is evaporated at room temperature under high vacuum. The organics are extracted from the water three times with 50 ml. of chloroform. The chloroform extracts are combined, dried (magnesium sulfate) and the solvent is removed to give crude 25-fluoro-1α-hydroxycholest-5-ene. 25-Fluoro-1α-hydroxycholest-5-ene can be purified by chromatographing the crude product on a silica gel column using a solvent of petroleum ether and diethyl ether.

Workup

  1. dissolutionabove is dissolved in 100 ml
  2. temperatureat reflux
  3. customto evaporate
  4. additionof water is added
  5. customThe tetrahydrofuran is evaporated at room temperature under high vacuum
  6. extractionThe organics are extracted from the water three times with 50 ml
  7. dry with materialdried (magnesium sulfate)
  8. customthe solvent is removed

Sources & evidence

ORD record
ord-76e449dbc4ef48d5b842cfaf6f0419ad
Source dataset
uspto-grants-1978_01
Patent number
US04069321

Reaction notes

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