Sodium Azide → (+/-)-(4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methyl azide
Reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[O:17][C:16]3[C:18]4[CH2:19][CH2:20][CH2:21][C:22]=4[CH:23]=[C:24]([Cl:25])[C:15]=3[CH2:14]2)(=O)=O)=CC=1.[N-:26]=[N+:27]=[N-:28].[Na+]>>[Cl:25][C:24]1[C:15]2[CH2:14][CH:13]([CH2:12][N:26]=[N+:27]=[N-:28])[O:17][C:16]=2[C:18]2[CH2:19][CH2:20][CH2:21][C:22]=2[CH:23]=1Participants
Procedure
Treatment of (±)-(4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methyl 4-methylbenzenesulfonate (4.0 g, 10.6 mmol) with sodium azide (2.75 g, 42.2 mmol) generally according to the procedure described for Intermediate 24 gave (±)-(4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methyl azide. Treatment of the azide with sulfided platinum on carbon (5 wt. %, 0.63 g) followed by hydrogen chloride (3 mL, 4 M in isopropanol) generally according to the procedure described for Example 2 provided 2.1 g (76%) of (±)-1-(4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine as a white solid, hydrochloride salt. mp 251-254° C.; Anal. calcd. for C12H14ClNOHCl: C, 55.40; H, 5.81; N, 5.38. Found: C, 55.10; H, 5.68; N, 5.29.
Sources & evidence
- ORD record
- ord-8cc93e08faa54b818da883be8d505234
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728155B2
Reaction notes
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