Potassium Carbonate → (S)-1-(4-bromophenyl)-N-(2-(2-isopropyl-1,3-dioxolan-2-yl)ethyl)ethanamine

HRID 80981Notes

Reaction equation

HRID 80981 reaction equation
[CH:1]([C:4]1([CH2:9][CH2:10]OS(C)(=O)=O)[O:8][CH2:7][CH2:6][O:5]1)([CH3:3])[CH3:2].[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+]>CC#N>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]([NH:25][CH2:10][CH2:9][C:4]2([CH:1]([CH3:2])[CH3:3])[O:5][CH2:6][CH2:7][O:8]2)[CH3:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamineHCID 107051032-(2-Isopropyl-1,3-dioxolan-2-yl)ethyl methanesulfonate

Product 1

HCID 58109166(S)-1-(4-bromophenyl)-N-(2-(2-isopropyl-1,3-dioxolan-2-yl)ethyl)ethanamineYield 38%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methanesulfonic acid 2-(2-isopropyl-[1,3]dioxolan-2-yl)-ethyl ester (12 g, 50 mmol) and (S)-1-(4-bromophenyl)ethanamine (19.9 g, 100 mmol) in CH3CN (250 mL) was added K2CO3 (8 g, 58 mmol), and the mixture was refluxed for 10 h. The solution was filtered, and the filtrate was concentrated to afford the crude product, which was purified by column chromatography to give [(S)-1-(4-bromophenyl)-ethyl]-[2-(2-isopropyl-[1,3]dioxolan-2-yl)-ethyl]-amine (6.5 g, 38%).

Workup

  1. temperaturethe mixture was refluxed for 10 h
  2. filtrationThe solution was filtered
  3. concentrationthe filtrate was concentrated
  4. customto afford the crude product, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-abbecd99663840539e4f37761a82b03f
Source dataset
uspto-grants-2014_09
Patent number
US08846668B2

Reaction notes

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