Hydrochloric Acid → HCID 69134667, compound

HRID 1912743Notes

Reaction equation

HRID 1912743 reaction equation
C([O:3][C@@H:4]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[CH:6]([C:7](=[O:24])[CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C:13]2=[O:23])[CH2:5]1)=O.C([O-])([O-])=O.[K+].[K+].Cl>CO>[OH:3][C@@H:4]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[CH:6]([C:7](=[O:24])[CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C:13]2=[O:23])[CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 86651518HCID 86651518, compound

Product 1

HCID 69134667HCID 69134667, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3α-formyloxyandrostane-6,17-dione (2.20 g) in MeOH (100 mL), K2CO3 (2.70 g) was added and the mixture stirred at room temperature for 10 minutes, then HCl 1N (20 mL) was added, the phases were separated and the aqueous one extracted with EtOAc (2×). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness to give 3α-hydroxyandrostane-6,17-dione (quantitative yield), which was used in the next step without purification. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.35 (1H, d), 3.40 (1H, m), 2.40-0.95 (20H, m), 0.80 (3H, s), 0.69 (3H, s).

Workup

  1. customthe phases were separated
  2. extractionthe aqueous one extracted with EtOAc (2×)
  3. washThe combined organic extracts were washed with H2O
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-3853f9c3a07345e48238826659a3bf13
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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