[4-(4-Methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl azide → (+/-)-1-[4-(4-Methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]3[CH2:14][CH:15]([CH2:17][N:18]=[N+]=[N-])[O:16][C:12]=3[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1>[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]3[CH2:14][CH:15]([CH2:17][NH2:18])[O:16][C:12]=3[CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Treatment of (±)-(4-bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (5.0 g, 13.0 mmol), o-tolylboronic acid (2.66 g, 19.57 mmol), dichlorobis(tri-o-tolylphosphine)-palladium(II) (0.512 g, 0.651 mmol), and potassium carbonate (4.51 g, 32.63 mmol) generally according to the procedure described for Intermediate 37 provided 4.0 g (77%) of (±)-1-[4-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a yellow oil. Treatment of (±)-(4-bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (3.8 g, 9.63 mmol) with sodium azide (2.5 g, 38.53 mmol) generally according to the procedure described for Intermediate 98 gave 2.39 g (94%) of [4-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl azide. Treatment of the azide with palladium on carbon (0.239 g, 10 wt. %) generally according to the procedure described for Example 1 provided 2.3 g (93%) of (±)-1-[4-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 239-241° C.; Anal. calcd. for C16H17NOHCl: C, 69.69; H, 6.58; N, 5.08. Found: C, 69:36; H, 6.64; N, 4.93.
Sources & evidence
- ORD record
- ord-1d059bce255e4cd5a4f1dffffd9d6b46
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07435837B2
Reaction notes
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