1-Propanol → 6beta-n-Propoxy-3beta,5alpha-dihydroxycholestane

HRID 980792Notes

Reaction equation

HRID 980792 reaction equation
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:29])[CH2:14][CH2:15][C@@H:16]3[C@@:21]4([CH3:27])[CH2:22][CH2:23][C@H:24]([OH:26])[CH2:25][C@:20]54[O:28][C@H:19]5[CH2:18][C@H:17]3[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].FC(F)(F)C(O)=O.[CH2:37]([OH:40])[CH2:38][CH3:39]>>[CH2:37]([O:40][C@H:19]1[C@:20]2([OH:28])[C@:21]([CH3:27])([CH2:22][CH2:23][C@H:24]([OH:26])[CH2:25]2)[C@@H:16]2[C@H:17]([C@H:12]3[C@:13]([CH3:29])([CH2:14][CH2:15]2)[C@@H:9]([C@H:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7])[CH2:10][CH2:11]3)[CH2:18]1)[CH2:38][CH3:39]

Participants

4

Reactant 3

HCID 10311-PropanolHCID 6422Trifluoroacetic acidHCID 2270375alpha,6alpha-Epoxycholesterol

Product 1

HCID 186064676beta-n-Propoxy-3beta,5alpha-dihydroxycholestane

Procedure

In a flask (50 ml) fitted with a condenser cholesterol 5α,6α-epoxide (100 mg., 0.25 mmol) in 1-propanol (20 ml) solution containing trifluoroacetic acid (1.0 ml) is refluxed for 1 hour. With vacuum evaporation the solvent is removed. The oily residue is dissolved in benzene (10 ml), extracted with 5% aqueous sodium bicarbonate (2 ml×2) and with water, and dried with anhydrous sodium sulfate. After vacuum evaporation the amorphous solid residue is purified by silica gel G-60 column liquid chromatography employing chloroform-methanol gradient elution. Selected fractions provide the product, 6β-n-propoxy-3β,5α-dihydroxycholestane. (45 mg).

Workup

  1. temperatureis refluxed for 1 hour
  2. customWith vacuum evaporation the solvent
  3. customis removed
  4. dissolutionThe oily residue is dissolved in benzene (10 ml)
  5. extractionextracted with 5% aqueous sodium bicarbonate (2 ml×2) and with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customAfter vacuum evaporation the amorphous solid residue
  8. customis purified by silica gel G-60 column liquid chromatography
  9. washchloroform-methanol gradient elution

Sources & evidence

ORD record
ord-7658c66d16ee4ae3874d81a8677f61d4
Source dataset
uspto-grants-1987_01
Patent number
US04639420

Reaction notes

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