2-(2-Nitrophenyl)-2,3-dihydrofuran → 2-Tetrahydrofuran-2-yl-aniline

HRID 447258Notes

Reaction equation

HRID 447258 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH:14]=[CH:13][CH2:12][O:11]1)([O-])=O.[N+](C1C=CC=CC=1C1CC=CO1)([O-])=O>>[O:11]1[CH2:12][CH2:13][CH2:14][CH:10]1[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:1]

Participants

3

Reactant 2

HCID 681084132-(2-Nitrophenyl)-2,3-dihydrofuranHCID 681087852-(2-Nitrophenyl)-2,5-dihydrofuran

Product 1

HCID 681089912-Tetrahydrofuran-2-yl-aniline

Procedure

3a and 3b were carried through the reduction step to afford 2-tetrahydrofuran-2-yl-aniline (4) as set forth in Example 1.b (below). Analysis of this material revealed that both 3a and 3b were formed with the same major enantiomer, with an overall 70% ee. It is unknown whether the absolute stereochemistry of the major enantiomer was (R) or (S).

Sources & evidence

ORD record
ord-d00cf220072e41e89d6db653ead16e86
Source dataset
uspto-grants-2013_07
Patent number
US08481552B2

Reaction notes

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