Benzyl chloroformate → (+/-)-Benzyl (7-tert-butyl-5-methoxy-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate

HRID 2115929Notes

Reaction equation

HRID 2115929 reaction equation
[C:1]([C:5]1[C:13]2[O:12][CH:11]([CH2:14][NH2:15])[CH2:10][C:9]=2[CH:8]=[C:7]([O:16][CH3:17])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>>[CH2:31]([O:30][C:28](=[O:29])[NH:15][CH2:14][CH:11]1[CH2:10][C:9]2[CH:8]=[C:7]([O:16][CH3:17])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:13]=2[O:12]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 68961710(+/-)-(7-Tert-butyl-5-methoxy-2,3-dihydro-1-benzofuran-2-yl)methylamine

Product 1

HCID 86629092(+/-)-Benzyl (7-tert-butyl-5-methoxy-2,3-dihydro-1-benzofuran-2-yl)methylcarbamateYield 85.5%

Procedure

Treatment of (±)-(7-tert-butyl-5-methoxy-2,3-dihydro-1-benzofuran-2-yl)methylamine (1.03 g, 3.8 mmol) with diisopropylethylamine (0.735 g, 5.7 mmol) and benzyl chloroformate (0.711 g, 4.2 mmol) generally according to the procedure described for Intermediate 12 gave 1.2 g (59%) of (±)-benzyl(7-tert-butyl-5-methoxy-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate as a colorless oil. Rf=0.51 (silica, ethyl acetate:hexanes 2:8); Anal. calcd. for C22H27NO4 C, 71.52; H, 7.37; N, 3.79. Found C, 71.2; H, 7.44; N, 3.77.

Sources & evidence

ORD record
ord-4fa3bfbb6d0e43eba5932bc124c50bee
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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