Trimethylsilyl iodide → HCID 11960868, compound

HRID 2116207Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl: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.I[Si](C)(C)C>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl: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

Reactant 2

HCID 85247Trimethylsilyl iodide

HCID 86599141HCID 86599141, compound

Product 1

HCID 11960868HCID 11960868, compoundYield 85%

Procedure

Treatment of (+)-benzyl {[7-(2,4-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate (2.06 g, 4.81 mmol) with iodotrimethylsilane (3.85 g, 19.24 mmol) generally according to the procedure described for Example 129 gave 0.933 g (85%) of (−)-1-[7-(2,4-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. [α]D25=−3.34 (c 10.0 in dimethylsulfoxide); mp 203-206° C.; Anal. calcd. for C15H13Cl2NOHCl: C, 54.59; H, 4.27; N, 4.24. Found: C, 53.69; H, 3.96; N, 3.99.

Sources & evidence

ORD record: ord-d5936dbccbf5454085268d41a7a61a3a
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435837B2

Reaction notes

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