HCID 86599145, compound → HCID 11961033, compound

HRID 2116206Notes

Reaction equation

HRID 2116206 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:17]2[O:16][CH:15]([CH2:18][NH:19]C(=O)OCC3C=CC=CC=3)[CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1>[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:17]2[O:16][CH:15]([CH2:18][NH2:19])[CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 86599145HCID 86599145, compound

Product 1

HCID 11961033HCID 11961033, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (−)-benzyl {[7-(2,4-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate (0.612 g, 1.55 mmol) with palladium on carbon (0.061 g, 10 wt. %) generally according to the procedure described for Example 1 gave 0.268 g (66%) of (−)-1-[7-(2,4-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. [α]D25=−4.66 (c 10.0 in dimethylsulfoxide); mp 222-224° C.; Anal. calcd. for C15H13F2NOHCl: C, 60.51; H, 4.74; N, 4.7. Found: C, 60.34; H, 4.58; N, 4.48.

Sources & evidence

ORD record
ord-bcf2ecee0d4e429583c614002a13e1c4
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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