Benzyl chloroformate → HCID 86599133, compound

HRID 2116031Notes

Reaction equation

HRID 2116031 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[O:15][CH:14]([CH2:17][NH2:18])[CH2:13][C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=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]>>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[O:15][CH:14]([CH2:17][NH:18][C:29](=[O:30])[O:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:13][C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11960770HCID 11960770, compound

Product 1

HCID 86599133HCID 86599133, compoundYield 94%

Procedure

Treatment of (±)-1-[7-(3-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine (798 g, 6.382.86 mmol) with diisopropylethylamine (0.554 g, 4.29 mmol) followed by benzyl chloroformate (0.536 g, 3.14 mmol) generally according to the procedure described for Intermediate 12 provided 1.01 g (94%) of (±)-benzyl {[7-(3-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate as a white solid. Rf=0.41 (silica, ethyl acetate:hexanes 2:8); Anal. calcd. for C23H20FNO3: C, 73.2; H, 5.34; N, 3.71. Found: C, 72.96H, 5.38; N, 3.59. Chiral HPLC separation of (±)-benzyl {[7-(3-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate (Chiralpak OD, isopropanol:hexane 2:8) provided two fractions. Fraction 1 (Rt=7.675 min, Chiralpak OD, isopropanol:hexane 2:8); Fraction 2 (Rt=9.182 min, Chiralpak OD, isopropanol:hexane 2:8).

Sources & evidence

ORD record
ord-5f50dbe4720d4f05b762a8b1dd140b19
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

Loading…