(+/-)-[4-(2,6-Dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl azide → (+/-)-1-[4-(2,6-Dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[C:14]2[CH2:15][CH:16]([CH2:18][N:19]=[N+]=[N-])[O:17][C:13]=2[CH:12]=[CH:11][CH:10]=1>[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[C:14]2[CH2:15][CH:16]([CH2:18][NH2:19])[O:17][C:13]=2[CH:12]=[CH:11][CH:10]=1Participants
3
Procedure
Treatment of (±)-[4-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (2.27 g, 5.55 mmol) with sodium azide (1.44 g, 22.23 mmol) generally according to the procedure described for Intermediate 98 gave 1.41 g (91%) of (±)-[4-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl azide. Treatment of the azide with palladium on carbon (0.141 g, 10 wt. %) generally according to the procedure described for Example 1 provided 1.36 g (93%) of (±)-1-[4-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 254-256° C.; Anal. calcd. for C17H19NOHCl: C, 70.46; H, 6.96; N, 4.83. Found: C, 69.03; H, 7.05; N, 4.66.
Sources & evidence
- ORD record
- ord-1c820a253da34add9e98ab11026d94f8
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07435837B2
Reaction notes
Loading…