HCID 86599143, compound → HCID 11961032, compound

HRID 2116201Notes

Reaction equation

HRID 2116201 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[C:19]2[O:18][CH:17]([CH2:20][NH:21]C(=O)OCC3C=CC=CC=3)[CH2:16][C:15]=2[CH:14]=[CH:13][CH:12]=1>[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[C:19]2[O:18][CH:17]([CH2:20][NH2:21])[CH2:16][C:15]=2[CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 86599143HCID 86599143, compound

Product 1

HCID 11961032HCID 11961032, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (+)-benzyl {[7-(2,4-dimethoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate (0.660 g, 1.57 mmol) with palladium on carbon (0.066 g, 10 wt. %) generally according to the procedure described for Example 1 afforded 0.242 g (48%) of (−)-1-[7-(2,4-dimethoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a pale yellow solid, hydrochloride salt. [α]D25=−4.7 (c 10.0 in methanol); mp 166-168° C.; Anal. calcd. for C17H19NO3HCl: C, 63.45; H, 6.26; N, 4.35. Found: C, 60.84; H, 6.51; N, 3.98.

Sources & evidence

ORD record
ord-e0bfd62e868b4f7aa2da0b505057432b
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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