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

HRID 2115954Notes

Reaction equation

HRID 2115954 reaction equation
[F: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.C(N(C(C)C)CC)(C)C.Cl[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30]>>[CH2:32]([O:31][C:29](=[O:30])[NH:18][CH2:17][CH:14]1[CH2:13][C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[C:16]=2[O:15]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11960765(+/-)-1-[7-(2-Fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine

Product 1

HCID 131727103(+/-)-Benzyl[7-(2-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamateYield 84%

Procedure

Treatment of (±)-1-[7-(2-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine (1.5 g, 5.36 mmol) with diisopropylethylamine (1.04 g, 8.04 mmol) and benzyl chloroformate (1.01 g, 5.89 mmol) generally according to the procedure described for Intermediate 12 afforded 1.7 g (84%) of (±)-benzyl[7-(2-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate as a colorless oil Rf=0.68 (silica, ethyl acetate:hexanes 1:9); Anal. calcd. for C22H18FNO3: C, 72.72; H, 4.99; N, 3.85. Found: C, 72.65H, 5.41; N, 3.47. Chiral HPLC separation of (±)-benzyl[7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate (Chiralcel OJ, hexane:isopropanol 9:1) provided two fractions. Fraction 1 (Rt=13.628 min, Chiralcel OJ, hexane:isopropanol 9:1); Fraction 2 (Rt=17.247 min, Chiralcel OJ, hexane:isopropanol 9:1).

Sources & evidence

ORD record
ord-3ae5ca68e9bc4b6dbb9a0e6e650c816b
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

Loading…