1-Propanol → 2beta-Propyloxy-3alpha-hydroxy-5alpha-pregnan-20-one

HRID 232811Notes

Reaction equation

HRID 232811 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:20]([CH3:22])([CH2:21][C@@H:2]12)[C@@H:19]1[C@H:8]([C@H:9]2[C@:16]([CH3:23])([CH2:17][CH2:18]1)[C@@H:12]([C:13](=[O:15])[CH3:14])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.C(=O)(O)[O-].[Na+].[CH2:29]([OH:32])[CH2:30][CH3:31]>S(=O)(=O)(O)O>[CH2:29]([O:32][C@H:2]1[CH2:21][C@@:20]2([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:19]2[CH2:18][CH2:17][C@@:16]2([CH3:23])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:13](=[O:15])[CH3:14])[CH2:4][C@@H:3]1[OH:1])[CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 10311-Propanol2×HCID 516892Sodium BicarbonateHCID 543466312alpha,3alpha-Epoxy-5alpha-pregnan-20-one

Product 1

HCID 700847912beta-Propyloxy-3alpha-hydroxy-5alpha-pregnan-20-oneYield 50%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

2α,3α-Epoxy-5α-pregnan-20-one (360 mg) was dissolved in 80 mL of propanol and cooled to °C. and added to a cold 1.0 mL propanol solution containing 5-drops of concentrated sulfuric acid. This reaction mixture was stirred for 30 minutes at this temperature and an additional 30 minutes at room temperature, poured into a 20% sodium bicarbonate solution and washed several times with chloroform. The combined organic phase was dried over potassium carbonate and concentrated. Purification of the crude product on a silica gel column eluting with hexane/ethyl acetate (70:30) gave the titled compound (206 mg, 50% yield) as white crystals.

Workup

  1. temperaturecooled to °C
  2. washwashed several times with chloroform
  3. dry with materialThe combined organic phase was dried over potassium carbonate
  4. concentrationconcentrated
  5. customPurification of the crude product on a silica gel column
  6. washeluting with hexane/ethyl acetate (70:30)

Sources & evidence

ORD record
ord-c6f48009daa7484e80d15711681def1b
Source dataset
uspto-grants-1997_01
Patent number
US05591733

Reaction notes

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