Potassium Bromide → HCID 9797346, compound

HRID 361314Notes

Reaction equation

HRID 361314 reaction equation
[CH2:1]([C@H:4]1[C@:21]2(O)[C@:16]([CH3:24])([CH2:17][CH2:18][C:19](=[O:23])[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:25])[CH2:9][CH2:8]3)[CH2:5]1)[C:2]#[CH:3].C1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](CC[C@]5(O)[C@]4(C)CCCC5)[C@@H]2C3)C)O1.[K+].[Br-]>CC(C)=O.C(OCC)(=O)C>[CH2:1]([C@H:4]1[C:21]2[C@:16]([CH3:24])([CH2:17][CH2:18][C:19](=[O:23])[CH: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:25])[CH2:9][CH2:8]3)[CH2:5]1)[C:2]#[CH:3]

Participants

6

Reactant 3

HCID 253877Potassium BromideHCID 10854804HCID 10854804, compoundHCID 86753640HCID 86753640, compound

Product 1

HCID 9797346HCID 9797346, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

6β-Propargyl-5α-hydroxyandrostane-3,17-dione (10). The 6β-propargyl bisketal 8 (0.6 mmol) was dissolved in acetone (30 ml) and p-TSOH (5 mg) was added. The reaction mixture was stirred at room temperature for 3 hours, diluted with ethyl acetate, washed (5% NaHCO3, brine, water) and dried. The ethyl acetate was removed in vacuo and the product was purified by column chromatography to yield the dione 90% yield; m.p. 145°-146° C.; IR (KBr) 3475 (C C--H), 3300 (OH), 2100, 1735 and 1715 (C=O) cm-1 ; 1H-NMR (CDCl3) δ 0.91 (s, 3H, 18-CH3), 1.21 (s, 3H 19-CH3), 3.0 (d, 1H, 4β-H).

Workup

  1. additionp-TSOH (5 mg) was added
  2. washwashed (5% NaHCO3, brine, water)
  3. customdried
  4. customThe ethyl acetate was removed in vacuo
  5. customthe product was purified by column chromatography
  6. customto yield the dione 90% yield

Sources & evidence

ORD record
ord-8f97c3f1864e40b4ab223bbc3ce56383
Source dataset
uspto-grants-1999_02
Patent number
US05866558

Reaction notes

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