Potassium Carbonate → 1-((S)-1-(4-bromophenyl)ethylamino)-5-methyl-3-phenylhex-5-en-3-ol

HRID 406726Notes

Reaction equation

HRID 406726 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([OH:9])[CH2:5][C:6]([CH3:8])=[CH2:7].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]([NH2:25])[CH3:24])=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]([NH:25][CH2:2][CH2:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([OH:9])[CH2:5][C:6]([CH3:8])=[CH2:7])[CH3:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamineHCID 595323881-Chlor-5-methyl-3-phenylhex-5-en-3-ol

Product 1

HCID 596356651-((S)-1-(4-bromophenyl)ethylamino)-5-methyl-3-phenylhex-5-en-3-olYield 60.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
96 °C

Procedure

1-chloro-5-methyl-3-phenylhex-5-en-3-ol (1.28 g, 5.7 mmol), (S)-1-(4-bromophenyl)ethanamine (1.37 g, 1.2 equiv), KI (995 mg, 1.05 equiv), K2CO3 (1.57 g, 2 equiv) were mixed with acetonitrile (15 mL) and heated to reflux (oil bath 96° C.) for overnight. After being cooled to rt, the mixture was filtered, concentrated, and purified by chromatography on a 40-g silica gel column, eluted with 0-8% MeOH in CH2Cl2, to afford 1-((S)-1-(4-bromophenyl)ethylamino)-5-methyl-3-phenylhex-5-en-3-ol (1.33 g, 60%).

Workup

  1. temperatureheated
  2. temperatureAfter being cooled to rt
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated
  5. custompurified by chromatography on a 40-g silica gel column
  6. washeluted with 0-8% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-271bd2a863c7410db02aa2d99a0f2dc8
Source dataset
uspto-grants-2014_06
Patent number
US08754076B2

Reaction notes

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