(+/-)-2-(Azidomethyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzofuran → (+/-)-[7-(4-Methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
Reaction equation
[N:1]([CH2:4][CH:5]1[CH2:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)[C:7]=2[O:6]1)=[N+]=[N-]>[Pd]>[CH3:20][C:17]1[CH:16]=[CH:15][C:14]([C:13]2[C:7]3[O:6][CH:5]([CH2:4][NH2:1])[CH2:9][C:8]=3[CH:10]=[CH:11][CH:12]=2)=[CH:19][CH:18]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Treatment of (±)-[7-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (1.01 g, 2.56 mmol) with sodium azide (0.664 g, 10.24 mmol) generally according to the procedure described for Intermediate 98 gave (±)-2-(azidomethyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.03 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.528 g (75%) of (±)-1-[7-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 231-232° C.; Anal. calcd. for C16H17NOHCl: C, 69.69; H, 6.58; N, 5.08. Found: C, 66.26; H, 7.0; N, 4.73.
Sources & evidence
- ORD record
- ord-96386cf1ddfd4ad794b9f5d0ad44b2ef
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07435837B2
Reaction notes
Loading…