(+)-benzyl (5-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate → HCID 11480921, compound

HRID 13962Notes

Reaction equation

HRID 13962 reaction equation
C[C:2]1[C:25]2[CH2:24][CH2:23][CH2:22][C:21]=2[C:5]2[O:6][CH:7]([CH2:9][NH:10]C(=O)OCC3C=CC=CC=3)[CH2:8][C:4]=2[CH:3]=1>[Pd]>[O:6]1[CH:7]([CH2:9][NH2:10])[CH2:8][C:4]2[CH:3]=[CH:2][C:25]3[CH2:24][CH2:23][CH2:22][C:21]=3[C:5]1=2

Participants

3

Reactant 1

HCID 86598548(+)-benzyl (5-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate

Product 1

HCID 11480921HCID 11480921, compoundYield 110.6%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (−)-benzyl (5-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate (1.39 g, 4.12 mmol) with palladium on carbon (10 wt. %, 0.139 g) generally according to the procedure described for Example 2 afforded 0.862 g (87%) of (−)-1-(3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine as a white solid, hydrochloride salt. [α]D25=+48.6 (c 10.0 in methanol); mp>220° C.; Anal. calcd. for C13H17NOHCl.0.1H2O: C, 64.64; H, 7.59; N, 5.80. Found: C, 64.62; H, 7.66; N, 5.77.

Sources & evidence

ORD record
ord-19e978b496434aa38d539876b193db40
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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