Benzyl chloroformate → (+)-Benzyl[7-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate

HRID 2116038Notes

Reaction equation

HRID 2116038 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=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]>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([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:6][CH:7]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11960864(+/-)-[7-(4-Methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine

Product 1

HCID 86599135(+)-Benzyl[7-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamateYield 56%

Procedure

Treatment of (±)-1-[7-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine (5.8 g, 24.24 mmol) with diisopropylethylamine (4.69 g, 36.35 mmol) followed by benzyl chloroformate (5.17 g, 30.30 mmol) generally according to the procedure described for Intermediate 12 provided 5.05 g (56%) of (±)-benzyl {[7-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate as a clear oil. Anal. calcd. for C24H23NO3: C, 77.19; H, 6.21; N, 3.75. Found: C, 76.97; H, 5.99; N, 3.68. Chiral HPLC separation of (±)-benzyl {[7-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate (Chiralpak OD, methanol:carbon dioxide 1:1) provided two fractions. Fraction 1 (Rt=3.735 min, Chiralpak OD, methanol:carbon dioxide 1:1); Fraction 2 (Rt=4.381 min, Chiralpak OD, methanol:carbon dioxide 1:1).

Sources & evidence

ORD record
ord-5c80e95cd2874d038303ee22a7ddc7b7
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

Loading…