Sodium Azide → (+/-)-2-(Azidomethyl)-5-methoxy-2,3,6,7,8,9-hexahydro-6,9-ethanonaphtho[1,2-b]furan
Reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[O:17][C:16]3[C:18]4[CH:19]5[CH2:29][CH2:28][CH:22]([C:23]=4[C:24]([O:26][CH3:27])=[CH:25][C:15]=3[CH2:14]2)[CH2:21][CH2:20]5)(=O)=O)=CC=1.[N-:30]=[N+:31]=[N-:32].[Na+]>>[N:30]([CH2:12][CH:13]1[O:17][C:16]2[C:18]3[CH:19]4[CH2:29][CH2:28][CH:22]([C:23]=3[C:24]([O:26][CH3:27])=[CH:25][C:15]=2[CH2:14]1)[CH2:21][CH2:20]4)=[N+:31]=[N-:32]Participants
3
Procedure
Treatment of (±)-(5-methoxy-2,3,6,7,8,9-hexahydro-6,9-ethanonaphtho[1,2-b]furan-2-yl)methyl 4-methylbenzenesulfonate (5.45 g, 13.1 mmol) with sodium azide (3.419 g, 52.6 mmol) generally according to the procedure described for Intermediate 24 gave (±)-2-(azidomethyl)-5-methoxy-2,3,6,7,8,9-hexahydro-6,9-ethanonaphtho[1,2-b]furan. Treatment of the azide with palladium on carbon (10 wt. %, 0.350 g) generally according to the procedure described for Example 2 gave 2.88 g (74%) of (±)-1-(5-methoxy-2,3,6,7,8,9-hexahydro-6,9-ethanonaphtho[1,2-b]furan-2-yl)methanamine as a white solid, hydrochloride salt. mp>210° C.; Anal. calcd. for C16H21NO2HCl: C, 64.97; H, 7.5; N, 4.74. Found: C, 64.71; H, 7.69; N, 4.54.
Sources & evidence
- ORD record
- ord-56a2eda4b0174f21b486b1223afa3121
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728155B2
Reaction notes
Loading…