1-Phenethylamine, (+)- → (R)-3-(1-phenylethylamino)methylenedihydrofuran-2-one

Reaction equation

[Na].O[CH:3]=[C:4]1[CH2:8][CH2:7][O:6][C:5]1=[O:9].[C:10]1([C@H:16]([NH2:18])[CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:10]1([C@H:16]([NH:18][CH:3]=[C:4]2[CH2:8][CH2:7][O:6][C:5]2=[O:9])[CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Reactant 2

HCID 6431891-Phenethylamine, (+)-

HCID 66988753HCID 66988753, compound

Product 1

HCID 66988015(R)-3-(1-phenylethylamino)methylenedihydrofuran-2-oneYield 71%

Procedure

Using 3-hydroxymethylenedihydrofuran-2-one sodium salt (50 mmol) and (R)-1-phenylethylamine (55 mmol) and proceeding according to the abovementioned method A1, (R)-3-(1-phenylethylamino)methylenedihydrofuran-2-one (7.70 g, efficiency: 71%) is produced in the form of a white powder.

Sources & evidence

ORD record: ord-0853b7b310a54b17a1c21a43e4ef34ed
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846125B2

Reaction notes

Loading…