1-Phenethylamine, (+)- → HCID 16225958, compound

HRID 2355233Notes

Reaction equation

HRID 2355233 reaction equation
F[C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C@H:17]([CH2:21]OS(C)(=O)=O)[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[C:27]1([C@H:33]([NH2:35])[CH3:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN1C(=O)CCC1>[C:4]1([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C@H:17]([CH2:21][NH:35][C@@H:33]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH3:34])[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 58869139HCID 58869139, compound

Product 1

HCID 16225958HCID 16225958, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

Methanesulfonic acid (R)-7-(3-fluoro-benzenesulfonyl)-chroman-2-ylmethyl ester (1.43 g, 3.7 mmol) and (R)-1-phenyl ethylamine (3 mL) were added to NMP (5 mL), and the reaction mixture was stirred for 18 hours at 110° C. The reaction mixture was cooled to room temperature, quenched by addition of water, and made basic to pH 14 by addition of 1M aqueous NaOH. The mixture was extracted with diethyl ether, and the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (0-30% EtOAc/hexanes) to give 1.2 g of (R)-(7-benzenesulfonyl-chroman-2-ylmethyl)-((R)-1-phenyl-ethyl)-aminel, MS (M+H)=408.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched by addition of water
  3. additionmade basic to pH 14 by addition of 1M aqueous NaOH
  4. extractionThe mixture was extracted with diethyl ether
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (0-30% EtOAc/hexanes)
  10. customto give 1.2 g of (R)-(7-benzenesulfonyl-chroman-2-ylmethyl)-((R)-1-phenyl-ethyl)-aminel, MS (M+H)=408

Sources & evidence

ORD record
ord-afcf70c40eeb406abfa6f9ce5cdac680
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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