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

HRID 2115934Notes

Reaction equation

HRID 2115934 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]2[CH2:14][CH:15]([CH2:17][NH2:18])[O:16][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:15]1[CH2:14][C:13]2[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])=[CH:9][CH:10]=[CH:11][C:12]=2[O:16]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 68961455(+/-)-1-[4-(2-Methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine

Product 1

HCID 91350502(+/-)-Benzyl[4-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamateYield 82%

Procedure

Treatment of (±)-1-[4-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine (0.533 g, 1.94 mmol) with diisopropylethylamine (0.375 g, 2.90 mmol) and benzyl chloroformate (0.363 g, 2.13 mmol) generally according to the procedure described for Intermediate 12 provided 0.594 g (82%) of (±)-benzyl[4-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate as colorless oil. Rf=0.42 (silica, ethyl acetate:hexanes 1:4); Anal. calcd. for C24H23NO3: C, 77.19H, 6.21; N, 3.75. Found: C, 76.0H, 6.01; N, 3.55. Chiral HPLC separation of (±)-benzyl[4-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate (Chiralcel OD, methanol) provided two fractions. Fraction 1 (Rt=5.952 min Chiralcel OD, methanol); Fraction 2 (Rt=7.345 min, Chiralcel OD, methanol).

Sources & evidence

ORD record
ord-3302a6e0d112478a8fee8af02f262077
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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