Hydrochloric Acid → HCID 86733138, compound

HRID 1606492Notes

Reaction equation

HRID 1606492 reaction equation
BrBr.[OH-:3].[Na+].[OH:5][C@:6]1([CH3:29])[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:22]2[C:21](=[O:27])[CH2:20][C@@:19]2(C)[C@H:12]3[CH2:13][CH2:14][C@@H:15]2C(=O)C)[CH2:7]1.Cl.O1[CH2:36][CH2:35][O:34][CH2:33]C1>O>[OH:5][C@:6]1([CH3:29])[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:22]2[C:21](=[O:27])[CH2:20][C@@:19]2([CH3:15])[C@H:12]3[CH2:13][CH2:14][C@@H:36]2[C:35]([O:34][CH3:33])=[O:3])[CH2:7]1

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 24408BromineHCID 312751,4-Dioxane2×HCID 70211040HCID 70211040, compound

Product 1

HCID 86733138HCID 86733138, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Bromine (0.54 ml.) was added to a solution of sodium hydroxide (1.5 g.) in water (13 ml.) at -5° over a period of 5 min. Cold dioxan (9 ml.) was then added and the resulting solution was added to a solution of 3α-hydroxy-3β-methyl-5α-pregnane-11,20-dione (1.0 g.) in dioxan (40 ml.) at 0°. The resulting mixture was kept at 5° for 1 hr., neutralised with concentrated hydrochloric acid and poured into water. Excess 2N-hydrochloric acid was then added and the precipitated solid was collected by filtration, dried in vacuo and dissolved in tetrahydrofuran (100 ml.). The resulting solution was treated with excess ethereal diazomethane at room temperature for 15 min. A few drops of acetic acid were then added and the mixture was partitioned between water and ether. The organic layer was washed with water, dried (MgSO4) and evaporated. Recrystallisation of the residue gave the title compound (0.49 g., 45%) as white needles, m.p. 150°; [α]D + 77° (c 1.0). (Found: C, 72.4; H, 9.2. C23H34O4 requires C, 72.7; H, 9.4%)

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customdried in vacuo
  3. dissolutiondissolved in tetrahydrofuran (100 ml.)
  4. additionThe resulting solution was treated with excess ethereal diazomethane at room temperature for 15 min
  5. additionA few drops of acetic acid were then added
  6. customthe mixture was partitioned between water and ether
  7. washThe organic layer was washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customRecrystallisation of the residue

Sources & evidence

ORD record
ord-8f046d7f6ef44766a0b21f737f43006b
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

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