1-Phenethylamine, (+)- → N-(1-Phenylethyl)amino-3-hydroxy-2,3,4,5-tetrahydrofuran

HRID 53942Notes

Reaction equation

HRID 53942 reaction equation
[O:1]1[C:6]2[CH2:5][O:4][CH2:3][C:2]1=2.[C:7]1([C@H:13]([NH2:15])[CH3:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C[Al](C)C>>[C:7]1([CH:13]([NH:15][CH:3]2[CH:2]([OH:1])[CH2:6][CH2:5][O:4]2)[CH3:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 6431891-Phenethylamine, (+)-HCID 16682925TrimethylaluminumHCID 220131503,4-Epoxy-2,5-dihydrofuran

Product 1

HCID 86750710N-(1-Phenylethyl)amino-3-hydroxy-2,3,4,5-tetrahydrofuran

Procedure

According to the procedure of Overman, et al. (J. Org. Chem. 1985, 50, 4154), 3,4-epoxy-2,5-dihydrofuran was treated with (R)-1-phenylethylamine and trimethylaluminum to give a 1:1 mixture of diastereomers. The mixture was purified by silica gel chromatography to provide the desired compound.

Workup

  1. customto give
  2. additiona 1:1 mixture of diastereomers
  3. customThe mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9af0bce2d775476eaf671bad4fa92694
Source dataset
uspto-grants-1997_04
Patent number
US05621109

Reaction notes

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