Ammonium Chloride → HCID 9924252, compound

HRID 1829630Notes

Reaction equation

HRID 1829630 reaction equation
[Si]([O:18][C@@H:19]1[CH2:36][CH2:35][C@@:34]2([CH3:37])[C@@H:21]([CH2:22][CH2:23][C@@H:24]3[C@@H:33]2[CH2:32][CH2:31][C@@:29]2([CH3:30])[C@H:25]3[CH2:26][CH2:27][C@@H:28]2[C:38]#[C:39][CH:40]([OH:42])[CH3:41])[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[NH4+].[Cl-]>O1CCCC1>[OH:42][CH:40]([CH3:41])[C:39]#[C:38][C@H:28]1[CH2:27][CH2:26][C@H:25]2[C@H:24]3[C@H:33]([CH2:32][CH2:31][C@:29]12[CH3:30])[C@:34]1([CH3:37])[C@H:21]([CH2:20][C@H:19]([OH:18])[CH2:36][CH2:35]1)[CH2:22][CH2:23]3

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 11215385HCID 11215385, compound

Product 1

HCID 9924252HCID 9924252, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4[3α-(t-butyidiphenylsilyloxy)-5α-androstan-17β-yl]-3-butyn-2-ol (30 mg, 0.052 mmol) in anhydrous tetrahydrofuran (2 mL) was treated with a 1M solution of (n-Bu)4N+F− (1.04 mL, 1.04 mmol) and the resulting solution was stirred at RT for 24 h. Addition of saturated aqueous NH4Cl solution was followed by extraction with ethyl acetate. The organic layer was extracted with water, brine and was dried with Na2SO4, and the solvent was evaporated in vacuo. Subsequent purification of the residue with flash column chromatography using methylene chloride/ethyl acetate 90/10 as eluent afforded the desired compound named above.

Workup

  1. extractionwas followed by extraction with ethyl acetate
  2. extractionThe organic layer was extracted with water, brine
  3. dry with materialwas dried with Na2SO4
  4. customthe solvent was evaporated in vacuo
  5. customSubsequent purification of the residue with flash column chromatography

Sources & evidence

ORD record
ord-fb925ac97fe842d396cfc41dcf1d6eb7
Source dataset
uspto-grants-2006_06
Patent number
US07064116B2

Reaction notes

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