Sodium Hydroxide → HCID 131719445, compound

HRID 1733907Notes

Reaction equation

HRID 1733907 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[Mg].[C:17]([N:25]1[CH2:34][CH2:33][C@H:32]2[C@@H:27]([CH2:28][CH2:29][C:30](=[O:35])[CH2:31]2)[CH2:26]1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-].[NH4+].[OH-].[Na+]>C1COCC1>[C:17]([N:25]1[CH2:34][CH2:33][C@H:32]2[C@@H:27]([CH2:28][CH2:29][C:30]([OH:35])([C:2]3[CH:7]=[CH:6][C:5]([O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])=[CH:4][CH:3]=3)[CH2:31]2)[CH2:26]1)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 4227167(4-Bromophenoxy)(tert-butyl)dimethylsilaneHCID 5462224MagnesiumHCID 12262834HCID 12262834, compound

Product 1

HCID 131719445HCID 131719445, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1-bromo-4-t-butyldimethylsilyloxy-benzene (1.7 g, 3.9 mmol), magnesium mesh (0.1 g, 3.9 mmol) and anhydrous THF were stirred at reflux temperature under a nitrogen atmosphere for 2 h. The reaction mixture was cooled to room temperature and transferred via syringe to a stirred semi-solution of trans-2-benzoyl-6-oxodecahydroisoquinoline (1.0 g, 3.9 mmol) in anhydrous THF at -78° C. The reaction mixture was warmed gradually to ambient temperature over 17.5 h. The reaction mixture was poured onto a saturated ammonium chloride solution, mixed, basified with a 1N NaOH solution and extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. Column chromatography (ethyl acetate) gave the product, a solid (747 mg): mp 103°-104° C.; NMR (CDCl3, 300 MHz): 7.5-7.3 (m, 7H), 6.85 (dd, 2H, J=8, 6), 4.9-4.6 (m, 1H), 3.9-3.55 (m, 1H), 3.1-2.4 (m, 2H), 1.9-1.0 (m, 9H), 0.95 (s, 9H), 0.25 (s, 3H), 0.2 (s, 3H); HRMS: Calcd: 465.2700, Found: 465.2689; Anal. Calcd for C28H39NO3Si: C, 72.23, H, 8.44, N, 3.01; Found: C, 71.99, H, 8.61, N, 2.87.

Workup

  1. temperatureat reflux temperature under a nitrogen atmosphere for 2 h
  2. temperatureThe reaction mixture was warmed gradually to ambient temperature over 17.5 h
  3. additionmixed
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customColumn chromatography (ethyl acetate) gave the product

Sources & evidence

ORD record
ord-efdcc1d9df434036a359e620af712e7e
Source dataset
uspto-grants-1996_07
Patent number
US05532243

Reaction notes

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