Potassium Carbonate → HCID 59190377, compound

HRID 219625Notes

Reaction equation

HRID 219625 reaction equation
BrC1C=CC([C@@H](N)C)=CC=1.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C@@H:18]([N:20]2[CH2:26][CH2:25][CH2:24][C:23]([CH2:33][C:34]([CH3:36])=[CH2:35])([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:22]C2=O)[CH3:19])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([C@@H:18]([NH:20][CH2:26][CH2:25][CH2:24][C:23]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([OH:22])[CH2:33][C:34]([CH3:36])=[CH2:35])[CH3:19])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamineHCID 59190391HCID 59190391, compound

Product 1

HCID 59190377HCID 59190377, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (S)-1-(4-bromo-phenyl)-ethyl amine (3.58 g, 0.018 mol) in dry CH3CN (350 mL) was added 3-((1S)-1-(4-bromophenyl)ethyl)-7-(2-methylallyl)-7-phenyl-1,3-oxazepan-2-one (4.2 g, 0.018 mol), KI (3.19 g, 0.019 mol), and K2CO3 (3.73 g, 0.027 mol). The mixture was stirred at reflux overnight, filtered, and concentrated to give the crude product, which was purified by column chromatography to give 7-((1S)-1-(4-bromophenyl)ethylamino)-2-methyl-4-phenylhept-1-en-4-ol (2.2 g, 30%) as an oil.

Workup

  1. temperatureat reflux overnight
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customto give the crude product, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-866cf1e4c35044579d28f1e177a45e92
Source dataset
uspto-grants-2012_06
Patent number
US08202857B2

Reaction notes

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