2,6-Lutidine → HCID 67856909, compound

HRID 1587037Notes

Reaction equation

HRID 1587037 reaction equation
[Si:1]([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][C@H:31]([OH:38])[C@@:29]2([CH3:30])[C@H:25]3[CH2:26][CH2:27][C:28]2=[O:39])[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:54]([CH3:57])([CH3:56])[CH3:55])(=O)=O>CCOCC>[Si:1]([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][C@H:31]([O:38][Si:54]([CH3:57])([CH3:56])[CH3:55])[C@@:29]2([CH3:30])[C@H:25]3[CH2:26][CH2:27][C:28]2=[O:39])[CH2:20]1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 65367Trimethylsilyl triflateHCID 67856969HCID 67856969, compound

Product 1

HCID 67856909HCID 67856909, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3α-tert-butyldiphenylsilyloxy-12α-hydroxy-5β-androstan-17-one (14.6 g) in ether (75 ml) is cooled to 0° C. and 2,6-lutidine (4.2 ml), trimethylsilyl trifluoromethanesulfonate (4.6 ml) are added and the mixture allowed to warm to room temperature, stirred for about 15 minutes, then diluted with ether. The organic solution was washed with dilute aqueous sodium bicarbonate, water and brine, then dried over magnesium sulfate, filtered, concentrated in vacuo, and the crude product purified by flash chromatography in 15% ether in hexane to give the desired product.

Workup

  1. washThe organic solution was washed with dilute aqueous sodium bicarbonate, water and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customthe crude product purified by flash chromatography in 15% ether in hexane

Sources & evidence

ORD record
ord-f622145440134bd0ab303640e1de2b81
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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