(+/-)-2-(Azidomethyl)-5-methoxy-2,3,6,7,8,9-hexahydro-6,9-ethanonaphtho[1,2-b]furan → (+/-)-1-(5-Methoxy-2,3,6,7,8,9-hexahydro-6,9-ethanonaphtho[1,2-b]furan-2-yl)methanamine
Reaction equation
[N:1]([CH2:4][CH:5]1[O:9][C:8]2[C:10]3[CH:11]4[CH2:21][CH2:20][CH:14]([C:15]=3[C:16]([O:18][CH3:19])=[CH:17][C:7]=2[CH2:6]1)[CH2:13][CH2:12]4)=[N+]=[N-]>[Pd]>[CH3:19][O:18][C:16]1[C:15]2[CH:14]3[CH2:20][CH2:21][CH:11]([CH2:12][CH2:13]3)[C:10]=2[C:8]2[O:9][CH:5]([CH2:4][NH2:1])[CH2:6][C:7]=2[CH:17]=1Participants
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-202a47c0f7134f9c88bf3abc44379d9b
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728155B2
Reaction notes
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