(2R*,6R*,9S*)-2-(azidomethyl)-5-methoxy-2,3,6,7,8,9-hexahydro-6,9-methanonaphtho[1,2-b]furan → HCID 11379585, compound
Reaction equation
[N:1]([CH2:4][C@@H:5]1[O:9][C:8]2[C:10]3[C@@H:11]4[CH2:20][C@H: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[CH:17]=[C:7]2[C:8](=[C:10]3[C:15]=1[CH:14]1[CH2:20][CH:11]3[CH2:12][CH2:13]1)[O:9][CH:5]([CH2:4][NH2:1])[CH2:6]2Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Treatment of [(2R*,6R*,9S*)-5-methoxy-2,3,6,7,8,9-hexahydro-6,9-methanonaphtho[1,2-b]furan-2-yl]methyl 4-methylbenzenesulfonate (1.2 g, 2.30 mmol) with sodium azide (0.78 g, 11.99 mmol) generally according to the procedure described for Intermediate 24 gave (2R*,6R*,9S*)-2-(azidomethyl)-5-methoxy-2,3,6,7,8,9-hexahydro-6,9-methanonaphtho[1,2-b]furan. Treatment of the azide with palladium on carbon (10 wt. %, 0.10 g) generally according to the procedure described for Example 2 gave 0.45 g (53%) of (9-methoxy-4-oxatetracyclo[9.2.1.02,10.03,7]tetradeca-2,7,9-trien-5-yl)methylamine as a white solid, hydrochloride salt. mp>200° C. (dec); Anal. calcd. for C16H21NO2HCl: C, 63.94; H, 7.15; N, 4.97. Found: C, 64.68; H, 7.63; N, 4.5. Separation of the stereoisomers of (9-methoxy-4-oxatetracyclo[9.2.1.02,10.03,7]tetradeca-2,7,9-trien-5-yl)methylamine provided three compounds with >99% optical purity.
Sources & evidence
- ORD record
- ord-365754f9773444679e94f8eedbc65109
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728155B2
Reaction notes
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