(+/-)-(5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methyl azide → (+/-)-1-(5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine
Reaction equation
[Cl: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>[Pt]>[Cl: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-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methyl 4-methylbenzenesulfonate (1.4 g, 3.70 mmol) with sodium azide (0.96 g, 14.78 mmol) generally according to the procedure described for Intermediate 24 gave (±)-(5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methyl azide as a crude oil. Treatment of the azide with sulfided platinum on carbon (5 wt. %, 0.15 g) generally according to the procedure described for Example 2 provided 0.74 g (77%) of (±)-1-(5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine as a white solid, hydrochloride salt. mp 270° C. (dec); Anal. calcd. for C12H14ClNOHCl: C, 55.4; H, 5.81; N, 5.38. Found: C, 55.4; H, 5.8; N, 4.91.
Sources & evidence
- ORD record
- ord-8013f3c6e53e4296bde256e5f84d842e
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728155B2
Reaction notes
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