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

HRID 80330Notes

Reaction equation

HRID 80330 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

3

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 66988753HCID 66988753, compound

Product 1

HCID 66988142(S)-3-(1-phenylethylamino)methylenedihydrofuran-2-oneYield 73%

Procedure

Using 3-hydroxymethylenedihydrofuran-2-one sodium salt (50 mmol) and (S)-1-phenylethylamine (55 mmol) and proceeding according to the abovementioned method A1, (S)-3-(1-phenylethylamino)methylenedihydrofuran-2-one (7.92 g, efficiency: 73%) is produced in the form of a white powder.

Sources & evidence

ORD record
ord-5b6a8e4101d749b691a34c0057d8db65
Source dataset
uspto-grants-2014_09
Patent number
US08846125B2

Reaction notes

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