(+/-)-2-(Azidomethyl)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan → (+/-)-1-(2,3,6,7,8,9-Hexahydronaphtho[1,2-b]furan-2-yl)methanamine

HRID 13958Notes

Reaction equation

HRID 13958 reaction equation
[N:1]([CH2:4][CH:5]1[O:9][C:8]2[C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=3[CH:16]=[CH:17][C:7]=2[CH2:6]1)=[N+]=[N-]>[Pd]>[O:9]1[CH:5]([CH2:4][NH2:1])[CH2:6][C:7]2[CH:17]=[CH:16][C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:8]1=2

Participants

3

Reactant 1

HCID 86598571(+/-)-2-(Azidomethyl)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan

Product 1

HCID 11241138(+/-)-1-(2,3,6,7,8,9-Hexahydronaphtho[1,2-b]furan-2-yl)methanamineYield 67%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethyl 4-methylbenzenesulfonate (2.05 g, 5.72 mmol) with sodium azide (0.929 g, 14.30 mmol) generally according to the procedure described for Intermediate 24 gave (±)-2-(azidomethyl)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan. Treatment of the azide with palladium on carbon (10 wt. %, 0.094 g) generally according to the procedure described for Example 2 afforded 0.917 g (67%) of (±)-1-(2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-yl)methanamine as a white solid, hydrochloride salt. mp>220° C. (dec.); Anal. calcd. for C13H17NOHCl.0.1H2O: C, 64.15; H, 7.50; N, 5.75. Found: C, 64.41; H, 7.64; N, 5.67.

Sources & evidence

ORD record
ord-7572676c5ca442e2968dd916d4734375
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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