HCID 11181172, compound → HCID 11773714, compound

HRID 1829628Notes

Reaction equation

HRID 1829628 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]2[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>O1CCCC1>[C:43]1([CH3:46])[CH:44]=[CH:45][C:40]([C:39]#[C:38][C@H:28]2[CH2:27][CH2:26][C@H:25]3[C@H:24]4[C@H:33]([CH2:32][CH2:31][C@:29]23[CH3:30])[C@:34]2([CH3:37])[C@H:21]([CH2:20][C@H:19]([OH:18])[CH2:36][CH2:35]2)[CH2:22][CH2:23]4)=[CH:41][CH:42]=1

Participants

3

Reactant 1

HCID 11181172HCID 11181172, compound

Product 1

HCID 11773714HCID 11773714, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3α-(t-butyldiphenylsilyloxy)-17β-[2-(4-tolyl)ethynyl]-5α-androstane (80 mg, 0.13 mmol) in anhydrous tetrahydrofuran (5.2 mL) was treated with a 1M solution of (n-Bu)4N+F− (2.6 mL, 2.6 mmol) and the resulting solution was stirred at RT for 48 h. Work up of the reaction was accomplished as in Example 2. Purification by flash column chromatography using dichloromethane as eluent afforded the desired product named above.

Workup

  1. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-a61625b10acd4f68894f223bf856b17a
Source dataset
uspto-grants-2006_06
Patent number
US07064116B2

Reaction notes

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