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

HRID 2116007Notes

Reaction equation

HRID 2116007 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][NH2:18])[CH2:13][C:12]=2[CH:11]=[C:10]([F:19])[CH:9]=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:18][CH2:17][CH:14]1[CH2:13][C:12]2[CH:11]=[C:10]([F:19])[CH:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:16]=2[O:15]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11288935(+/-)-1-[7-(2-Chlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanamine

Product 1

HCID 91164538(+)-Benzyl[7-(2-chlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate

Procedure

Treatment of (±)-1-[7-(2-chlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanamine (2.92 g, 10.5 mmol) with diisopropylethylamine (1.70 g, 13.1 mmol) and benzyl chloroformate (1.97 g, 11.6 mmol) generally according to the procedure described for Intermediate 12 provided 3.02 (70%) of (±)-benzyl[7-(2-chlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate as a colorless oil. Rf=0.76 (silica, ethyl acetate:hexanes 1:9); Anal. calcd. for C23H19ClFNO3.0.5H2O: C, 65.64; H, 4.79; N, 3.33. Found: C, 65.28; H, 4.73; N, 3.18. Chiral HPLC separation of (±)-benzyl[7-(2-chlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate (Chiralcel OJ, hexane:ethanol 1:1) provided two fractions. Fraction 1 (Rt=9.322 min, Chiralcel OJ, hexane:ethanol 1:1); Fraction 2 (Rt=13.646 min, Chiralcel OJ, hexane:ethanol 1:1).

Sources & evidence

ORD record
ord-2d67ae33389045f8b14d24c447e638ea
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

Loading…