HCID 86599134, compound → HCID 11960862, compound

HRID 2116194Notes

Reaction equation

HRID 2116194 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[O:16][CH:15]([CH2:18][NH:19]C(=O)OCC4C=CC=CC=4)[CH2:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1>[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[O:16][CH:15]([CH2:18][NH2:19])[CH2:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 86599134HCID 86599134, compound

Product 1

HCID 11960862HCID 11960862, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (−)-benzyl {[7-(3-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate (1.38 g, 3.54 mmol) with palladium on carbon (0.138 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.558 g (62%) of (−)-1-[7-(3-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. [α]D25=−32.14 (c 10.0 in methanol); mp 156-158° C.; Anal. calcd. for C16H17NO2HCl: C, 65.86; H, 6.22; N, 4.8. Found: C, 65.03; H, 6.22; N, 4.7.

Sources & evidence

ORD record
ord-7b5d136d50ec4a8f967fd9ab2a5606cb
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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