Trimethylsilyl iodide → HCID 11960769, compound

HRID 2116191Notes

Reaction equation

HRID 2116191 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[O:15][CH:14]([CH2:17][NH:18]C(=O)OCC3C=CC=CC=3)[CH2:13][C:12]=2[CH:11]=[CH:10][CH:9]=1.I[Si](C)(C)C>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[O:15][CH:14]([CH2:17][NH2:18])[CH2:13][C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86599242(+)-Benzyl{[7-(2-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate

Product 1

HCID 11960769HCID 11960769, compoundYield 85.8%

Procedure

Treatment of (−)-benzyl {[7-(2-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate (0.480 g, 1.22 mmol) with iodotrimethylsilane (0.975 g, 4.87 mmol) generally according to the procedure described for Example 129 afforded 0.272 g (75%) of (+)-1-[7-(2-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. [α]D25=+9.90 (c 10.0 in dimethylsulfoxide); mp 186-188° C.; Anal. calcd. for C15H14ClNOHCl: C, 60.83; H, 5.1; N, 4.73. Found C, 60.53; H, 5.39; N, 4.62.

Sources & evidence

ORD record
ord-6d276a0e63184ccbacfab87b9302801d
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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