(+/-)-(5-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methyl azide → (+/-)-1-(5-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine
Reaction equation
[CH3:1][C:2]1[C:17]2[CH2:16][CH2:15][CH2:14][C:13]=2[C:5]2[O:6][CH:7]([CH2:9][N:10]=[N+]=[N-])[CH2:8][C:4]=2[CH:3]=1>[Pd]>[CH3:1][C:2]1[C:17]2[CH2:16][CH2:15][CH2:14][C:13]=2[C:5]2[O:6][CH:7]([CH2:9][NH2:10])[CH2:8][C:4]=2[CH:3]=1Participants
3
Procedure
Treatment of (±)-(5-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methyl 4-methylbenzenesulfonate (0.862 g, 2.40 mmol) with sodium azide (0.469 g, 7.21 mmol) generally according to the procedure described for Intermediate 24 gave (±)-(5-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methyl azide. Treatment of the azide with palladium on carbon (10 wt. %, 0.055 g) generally according to the procedure described for Example 2 gave 0.460 g (80%) of (±)-1-(5-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine as a white solid, hydrochloride salt. mp>200° C. (dec.); Anal. calcd. for C13H17NOHCl: C, 65.13; H, 7.57; N, 5.84. Found: C, 64.97; H, 7.61; N, 5.67.
Sources & evidence
- ORD record
- ord-60424480f5d940f48d6f86480dd96c78
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728155B2
Reaction notes
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