HCID 11331470, compound → HCID 10271052, compound

HRID 1829626Notes

Reaction equation

HRID 1829626 reaction equation
[Br:1][C:2](Br)=[CH:3][C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:5]12[CH3:6])[C@:18]1([CH3:19])[C@H:13]([CH2:14][C@H:15]([O:23][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:16][CH2:17]1)[CH2:12][CH2:11]3>O1CCCC1>[Br:1][C:2]#[C:3][C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:5]12[CH3:6])[C@:18]1([CH3:19])[C@H:13]([CH2:14][C@H:15]([OH:23])[CH2:16][CH2:17]1)[CH2:12][CH2:11]3

Participants

3

Reactant 1

HCID 11331470HCID 11331470, compound

Product 1

HCID 10271052HCID 10271052, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,1-dibromo-2-[3α-(t-butyldiphenylsilyloxy)-5α-androstan-17β-yl]-ethylene (0.074 mmol) in anhydrous tetrahydrofuran (3 mL) was treated with a 1M solution of (n-Bu)4N+F− (1.48 mL, 1.48 mmol) and the resulting solution was stirred at RT for 48 h. The mixture was quenched with saturated aqueous NH4Cl solution. Ethyl acetate was added and the organic layer was extracted with water and brine and was dried (Na2SO4). Evaporation of the solvent in vacuo followed by purification of the residue with flash column chromatography using methylene chloridelethyl acetate 95/5 as eluent afforded the desired compound named above.

Workup

  1. customThe mixture was quenched with saturated aqueous NH4Cl solution
  2. additionEthyl acetate was added
  3. extractionthe organic layer was extracted with water and brine
  4. dry with materialwas dried (Na2SO4)
  5. customEvaporation of the solvent in vacuo
  6. customfollowed by purification of the residue with flash column chromatography

Sources & evidence

ORD record
ord-b9542d2c588a450d8961a4e8dc18c6b2
Source dataset
uspto-grants-2006_06
Patent number
US07064116B2

Reaction notes

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