HCID 69592544, compound → HCID 87903204, compound

HRID 1829635Notes

Reaction equation

HRID 1829635 reaction equation
C[Si](C)(C)[C:3]#[C:4][CH:5]([C@H:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:8]12[CH3:9])[C@:21]1([CH3:22])[C@H:16]([CH2:17][C@H:18]([O:26][Si:27]([C:40]([CH3:43])([CH3:42])[CH3:41])([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:19][CH2:20]1)[CH2:15][CH2:14]3)[OH:6]>C1COCC1>[Si:27]([O:26][C@@H:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[C@@H:16]([CH2:15][CH2:14][C@@H:13]3[C@@H:23]2[CH2:24][CH2:25][C@@:8]2([CH3:9])[C@H:10]3[CH2:11][CH2:12][C@@H:7]2[CH:5]([OH:6])[C:4]#[CH:3])[CH2:17]1)([C:40]([CH3:43])([CH3:42])[CH3:41])([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 1

HCID 69592544HCID 69592544, compound

Product 1

HCID 87903204HCID 87903204, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (n-Bu)4N+F− 1M in THF (0.72 mL, 0.72 mmol) was added to a solution of 3-trimethylsilyl-1-[3α-(t-butyidiphenylsilyloxy)-5α-androstan-17β-yl]-2-propyn-1-ol (310 mg, 0.48 mmol) in THF (10 mL) and the resulting mixture was stirred at RT for 30 min. The reaction mixture was worked up as in Example 7 to afford after purification by flash column chromatography using petroleum ether/acetone 82/18 as elution solvent the compound named above.

Workup

  1. customto afford
  2. customafter purification by flash column chromatography
  3. washas elution solvent the compound

Sources & evidence

ORD record
ord-ff773c2d3ba14ebab7fd436704b261c7
Source dataset
uspto-grants-2006_06
Patent number
US07064116B2

Reaction notes

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