Ammonia → HCID 70626502, compound

HRID 1834199Notes

Reaction equation

HRID 1834199 reaction equation
[O:1]1[CH:3]2[C:4](=[O:30])[CH:5]=[C:6]3[C@:27]([CH3:28])([CH:2]12)[C@@H:26]1[C@H:9]([C@H:10]2[C@:23]([CH3:29])([CH2:24][CH2:25]1)[C@@H:13]([C@H:14]([CH3:22])[CH2:15][CH2:16][CH2:17][C:18]([F:21])([CH3:20])[CH3:19])[CH2:12][CH2:11]2)[CH:8]=[CH:7]3.N.[Cl-].[NH4+].[Li]>O1CCCC1>[F:21][C:18]([CH2:17][CH2:16][CH2:15][C@H:14]([C@@H:13]1[C@:23]2([CH3:29])[C@H:10]([C@H:9]3[C@H:26]([CH2:25][CH2:24]2)[C@:27]2([CH3:28])[C:6]([CH2:5][C@H:4]([CH2:3][C@@H:2]2[OH:1])[OH:30])=[CH:7][CH2:8]3)[CH2:11][CH2:12]1)[CH3:22])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 53929283HCID 53929283, compound

Product 1

HCID 70626502HCID 70626502, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,2-Epoxy-25-fluoro-4,6-cholestadien-3-one (0.01 moles) prepared according to 1D above is dissolved in 100 ml. of a 1:1 solvent mixture of tetrahydrofuran and liquid ammonia containing 0.04 moles of ammonium chloride. The mixture is stirred at reflux using a dry ice condenser and reduced by adding 0.42 grams of finally divided metalic lithium (0.06 gm. atoms) over a period of 10 minutes. The mixture is refluxed for one hour after which time the ammonia is allowed to evaporate from the mixture. The solvent is removed from the remainder of the mixture by evaporation to near dryness at room temperature. The residue is washed in 50 ml of ice water containing 5.0 g of ammonium chloride. The ice water is extracted three times with 50 ml of chloroform. The chloroform extracts are combined and the solvent is removed by evaporation to yield crude 25-fluoro-1α-hydroxycholesterol. 25-Fluoro-1α-hydroxycholesterol 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 from the mixture
  4. customThe solvent is removed from the remainder of the mixture by evaporation
  5. customat room temperature
  6. washThe residue is washed in 50 ml of ice water containing 5.0 g of ammonium chloride
  7. extractionThe ice water is extracted three times with 50 ml of chloroform
  8. customthe solvent is removed by evaporation

Sources & evidence

ORD record
ord-f50f087e7fab4b26ad471ef6e735316f
Source dataset
uspto-grants-1978_01
Patent number
US04069321

Reaction notes

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