Water → HCID 69007680, compound

HRID 42084Notes

Reaction equation

HRID 42084 reaction equation
[N+:1]([O-:31])([O:3][C@@H:4]1[CH:21]2[C@:16]([CH3:22])([CH2:17][CH2:18][CH2:19][CH2:20]2)[C@@H:15]2[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C:10]24OCCO[C:9]2(OCC[O:23]4)[CH2:8]3)[CH2:5]1)=[O:2].CC1C=CC(S(O)(=O)=[O:40])=CC=1.O.C([O-])(O)=O.[Na+]>CC(C)=O>[N+:1]([O-:31])([O:3][C@@H:4]1[CH:21]2[C@:16]([CH3:22])([CH2:17][CH2:18][C:19](=[O:40])[CH2:20]2)[C@@H:15]2[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C:10](=[O:23])[CH2:9][CH2:8]3)[CH2:5]1)=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 86635563HCID 86635563, compound

Product 1

HCID 69007680HCID 69007680, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 3,3:17,17-bis(ethylendioxy)androstane-6α-yl nitrate (2.50 g) and pTSA.H2O (6.05 g) in acetone (150 mL) was stirred at room temperature for 1.5 h. The solution was neutralized by addition of 5% aqueous NaHCO3, and acetone was evaporated. The aqueous phase was extracted with CH2Cl2 (3×50 mL). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, cyclohexane/Acetone/CH2Cl2 70/15/15) to give the title compound II-ab as a white solid (1.66 g, 75%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 5.09 (1H, ddd), 2.60-0.95 (17H, m), 1.25 (3H, s), 0.90 (3H, s).

Workup

  1. customwas evaporated
  2. extractionThe aqueous phase was extracted with CH2Cl2 (3×50 mL)
  3. washThe combined organic extracts were washed with H2O
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography (SiO2, cyclohexane/Acetone/CH2Cl2 70/15/15)

Sources & evidence

ORD record
ord-f0a4f3cfe50545289c007eb866310695
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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