(+/-)-{7-[(1E)-3,3-dimethylbut-1-enyl]-2,3-dihydro-1-benzofuran-2-yl}methyl azide → HCID 68968241, compound

HRID 2116180Notes

Reaction equation

HRID 2116180 reaction equation
[CH3:1][C:2]([CH3:19])([CH3:18])/[CH:3]=[CH:4]/[C:5]1[C:13]2[O:12][CH:11]([CH2:14][N:15]=[N+]=[N-])[CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1>[Pd]>[CH3:1][C:2]([CH3:19])([CH3:18])[CH2:3][CH2:4][C:5]1[C:13]2[O:12][CH:11]([CH2:14][NH2:15])[CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

3

Reactant 1

HCID 86599236(+/-)-{7-[(1E)-3,3-dimethylbut-1-enyl]-2,3-dihydro-1-benzofuran-2-yl}methyl azide

Product 1

HCID 68968241HCID 68968241, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-{7-[(1E)-3,3-dimethylbut-1-enyl]-2,3-dihydro-1-benzofuran-2-yl}methyl azide (1.82 g, 7.07 mmol) with palladium on carbon (0.18 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.642 g (34%) of (±)-1-[7-(3,3-dimethylbutyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 158-160° C.; Anal. calcd. for C15H23NOHCl: C, 66.77; H, 8.97; N, 5.19. Found: C, 66.31; H, 8.56; N, 5.09.

Sources & evidence

ORD record
ord-97485337f0f54aa4858270dfadcbe507
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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