p-Toluenesulfonic acid → HCID 69134726, compound

HRID 1912734Notes

Reaction equation

HRID 1912734 reaction equation
C1(C)C=CC(S(O[C@H:11]2[CH2:28][CH2:27][C@@:26]3([CH3:29])[C:13](=[CH:14][CH2:15][C@@H:16]4[C@@H:25]3[CH2:24][CH2:23][C@@:21]3([CH3:22])[C@H:17]4[CH2:18][CH2:19][C:20]3=[O:30])[CH2:12]2)(=O)=O)=CC=1.[CH2:32]([OH:36])[CH2:33][CH2:34][OH:35].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>O>[OH:35][CH2:34][CH2:33][CH2:32][O:36][C@H:11]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C:13](=[CH:14][CH2:15][C@@H:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH2:19][C:20]2=[O:30])[CH2:12]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 516892Sodium BicarbonateHCID 13251127HCID 13251127, compound

Product 1

HCID 69134726HCID 69134726, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3β-(p-Toluensulfonyloxy)androst-5-en-17-one (12.00 g) was added to a suspension of propane-1,3-diol (61 mL) and PTSA (610 mg) at 95° C. After stirring for 40 minutes, the mixture was cooled to room temperature, and poured in water (800 mL), bringing the pH to 7 with 5% NaHCO3. After 3 hrs the solid was filtered and dissolved in CH2Cl2. The solution was dried over Na2SO4 and evaporated to dryness under reduced pressure to give 3β-(3-hydroxypropoxy)androst-5-en-17-one (9.10 g, 97%), used without further purification. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 5.35 (1H, m), 4.34 (1H, t), 3.43 (4H, m), 3.06 (1H, m), 2.45-0.85 (21H, m), 0.96 (3H, s), 0.79 (3H, s).

Workup

  1. filtrationAfter 3 hrs the solid was filtered
  2. dissolutiondissolved in CH2Cl2
  3. dry with materialThe solution was dried over Na2SO4
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b00b1302140243d894ce5f94093b7355
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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