Benzyl chloroformate → (+/-)-Benzyl[5-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate

HRID 2116006Notes

Reaction equation

HRID 2116006 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[C:5]2[O:9][CH:8]([CH2:10][NH2:11])[CH2:7][C:6]=2[CH:12]=1.C(N(C(C)C)CC)(C)C.Cl[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>>[CH2:33]([O:32][C:30](=[O:31])[NH:11][CH2:10][CH:8]1[CH2:7][C:6]2[CH:12]=[C:2]([F:1])[CH:3]=[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])[C:5]=2[O:9]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11960951(+/-)-1-[5-Fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine

Product 1

HCID 90753716(+/-)-Benzyl[5-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate

Procedure

Treatment of (±)-1-[5-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine (3.11 g, 12.1 mmol) with diisopropylethylamine (2.34 g, 18.1 mmol) and benzyl chloroformate (2.27 g, 13.3 mmol) generally according to the procedure described for Intermediate 12 gave 4.35 (92%) of (±)-benzyl[5-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate as a colorless oil. Rf=0.83 (silica, ethyl acetate:hexanes 1:9); Anal. calcd. for C24H22FO3.0.2H2O: C, 72.97; H, 5.72; N, 3.55. Found: C, 72.8; H, 5.72; N, 3.48. Chiral HPLC separation of (±)-benzyl[5-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate (Chiralcel OD, hexane:isopropanol 8:2) provided two fractions. Fraction 1 (Rt=7.269 min, Chiralcel OD, hexane:isopropanol 8:2); Fraction 2 (Rt=8.449 min, Chiralcel OD, hexane:isopropanol 8:2).

Sources & evidence

ORD record
ord-fa84aace64094b598d0201693b027078
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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