Water → HCID 10864189, compound

HRID 479311Notes

Reaction equation

HRID 479311 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([CH2:12][CH2:13][CH2:14][C@H:15]([C@@H:17]1[C@:34]2([CH3:35])[C@H:20]([C@H:21]3[C@H:31]([CH2:32][CH2:33]2)[C@:29]2([CH3:30])[C:24]([CH2:25][C@@H:26]([OH:36])[CH2:27][CH2:28]2)=[CH:23][CH2:22]3)[CH2:19][CH2:18]1)[CH3:16])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CN1CCCCC1=O.O>C1(C)C=CC=CC=1>[Si:1]([O:8][CH2:9][C@@H:10]([CH2:12][CH2:13][CH2:14][C@H:15]([C@@H:17]1[C@:34]2([CH3:35])[C@H:20]([C@H:21]3[C@H:31]([CH2:32][CH2:33]2)[C@:29]2([CH3:30])[C:24](=[CH:25][C:26](=[O:36])[CH2:27][CH2:28]2)[CH2:23][CH2:22]3)[CH2:19][CH2:18]1)[CH3:16])[CH3:11])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 13603N-Methyl-2-piperidoneHCID 11763027HCID 11763027, compound

Product 1

HCID 10864189HCID 10864189, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of (25R)-26-(tert-butyldimethylsilyloxy)cholest-5-en-3β-ol (7.4g, 14.3mmol) and 1-methylpiperidone (55 mL) in toluene (550 mL) was heated to reflux temperature and 100ml toluene was distilled off. Aluminium triisopropyl oxide (15 g, 1377 mmol) was then added portionwise over 10 minutes and the whole heated at refux for 4 hours. After cooling, water (300 mL) was added and the aqueous layer separated and extracted with diethyl ether (5×100 mL). The combined organic layers were washed with water (2×60 mL), dried over magnesium sulphate and concentrated to give residue which was purified by flash chromatography to give 6.26 g (25R)-26-(tert-Butyldimethylsilyloxy)-cholest-4-en-3-one (6.26 g).

Workup

  1. temperaturewas heated
  2. distillationwas distilled off
  3. temperaturethe whole heated at refux for 4 hours
  4. temperatureAfter cooling
  5. customthe aqueous layer separated
  6. extractionextracted with diethyl ether (5×100 mL)
  7. washThe combined organic layers were washed with water (2×60 mL)
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated
  10. customto give residue which
  11. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-dfce845a5f4e4efe863c6ff7dfc1b69e
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

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