Benzyl chloroformate → (+/-)-Benzyl{[4-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate

HRID 2116020Notes

Reaction equation

HRID 2116020 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]3[CH2:14][CH:15]([CH2:17][NH2:18])[O:16][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:13]3[CH2:14][CH:15]([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)[O:16][C:12]=3[CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 68961108(+/-)-1-[4-(4-Methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine

Product 1

HCID 86599130(+/-)-Benzyl{[4-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamateYield 90%

Procedure

Treatment of (±)-1-[4-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine (1.94 g, 7.03 mmol) with diisopropylethylamine (1.36 g, 10.55 mmol) followed by benzyl chloroformate (1.32 g, 7.74 mmol) generally according to the procedure described for Intermediate 12 provided 2.36 g (90%) of (±)-benzyl {[4-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate as a white solid. mp 134-136° C.; Anal. calcd. for C24H23NO3: C, 77.19; H, 6.21; N, 3.75. Found: C, 77.08; H, 6.3; N, 3.69.

Sources & evidence

ORD record
ord-bb6473ac6d3947a4b602196c0af4386b
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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