Water → HCID 9924154, compound

HRID 1829632Notes

Reaction equation

HRID 1829632 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][C:40](=[O:42])[CH3:41])[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.N1C=CC=CC=1.O>ClCCl>[O:42]=[C: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

5

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 86600184HCID 86600184, compound

Product 1

HCID 9924154HCID 9924154, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4[3α-(t-butyidiphenylsilyloxy)-5α-androstan-17β-yl]-3-butyn-2-one (40 mg, 0.07 mmol) in anhydrous dichloromethane (2.8 mL) was treated with HF pyridine (0.008 mL, 0.28 mmol) at 0° C. and the resulting mixture was stirred at RT for 2 h. Addition of water at 0° C. was followed by extraction with methylene chloride. The organic layer was washed with brine and was dried with Na2SO4 and the solvent was evaporated in vacuo. Subsequent purification of the residue with flash column chromatography using dichloromethane/ethyl acetate 95/5 as eluent afforded the desired compound named above.

Workup

  1. extractionwas followed by extraction with methylene chloride
  2. washThe organic layer was washed with 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-fc899a1ca06849d790c68046decb9efc
Source dataset
uspto-grants-2006_06
Patent number
US07064116B2

Reaction notes

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