Water → HCID 69873833, compound

HRID 479317Notes

Reaction equation

HRID 479317 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:33][C@@H:32]2[C@:19]([CH3:36])([CH2:20][CH2:21][C@H:22]3[C@H:31]2[CH2:30][CH:29]=[C:28]2[C@:23]3([CH3:35])[CH2:24][CH2:25][C@H:26]([OH:34])[CH2:27]2)[C@H:10]1[C@H:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])([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][C@H:9]1[CH2:33][C@@H:32]2[C@:19]([CH3:36])([CH2:20][CH2:21][C@H:22]3[C@H:31]2[CH2:30][CH2:29][C:28]2[C@:23]3([CH3:35])[CH2:24][CH2:25][C:26](=[O:34])[CH:27]=2)[C@H:10]1[C@H:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 13603N-Methyl-2-piperidoneHCID 69873851HCID 69873851, compound

Product 1

HCID 69873833HCID 69873833, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A mixture of 16β-(tert-butyldimethylsilyloxy)cholest-5-en-3β-ol (6.7 g, 12 mmol) and 1-methylpiperidone (25 mL) in toluene (500 mL) was heated to reflux temperature and 50 ml toluene was distilled off. Aluminium triisopropyl oxide (9.8 g, 48 mmol) in toluene (50 mL) was then added dropwise and the whole heated at refux for 4 hours. After cooling, water (200 mL) was added and the aqueous layer separated and extracted with diethyl ether. The combined organic layers were washed with water (100 mL), dried over magnesium sulphate and concentrated to give residue which was purified by recrystallization from methanol to give 16β-(tert-butyldimethylsilyloxy)cholest-4-en-3-one (5.4 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
  7. washThe combined organic layers were washed with water (100 mL)
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated
  10. customto give residue which
  11. customwas purified by recrystallization from methanol

Sources & evidence

ORD record
ord-ffd923f85fce4af482d4abbd38ce0410
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

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