Benzyl chloroformate → HCID 86601820, compound

HRID 2115918Notes

Reaction equation

HRID 2115918 reaction equation
[CH:1]([C:4]1[C:12]2[O:11][CH:10]([CH2:13][NH2:14])[CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>>[CH2:28]([O:27][C:25](=[O:26])[NH:14][CH2:13][CH:10]1[CH2:9][C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:12]=2[O:11]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 68966371HCID 68966371, compound

Product 1

HCID 86601820HCID 86601820, compoundYield 59%

Procedure

Treatment of (±)-(7-isopropyl-2,3-dihydro-1-benzofuran-2-yl)methylamine (2.2 g, 9.66 mmol) with diisopropylethylamine (3.12 g, 24.15 mmol) and benzyl chloroformate (1.81 g, 10.63 mmol) generally according to the procedure described for Intermediate 12 gave 1.2 g (59%) of (±)-benzyl(7-isopropyl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate as a colorless oil. Anal. calcd. for C20H23NO3 C, 73.82; H, 7.12; N, 4.3. Found C, 73.32; H, 7.33; N, 4.15. Chiral HPLC separation of (±)-benzyl(7-isopropyl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate (Chiralcel OJ, ethanol) provided two fractions. Fraction 1 (Rt=9.319 min, Chiralcel OJ, ethanol); Fraction 2 (Rt=11.868 min, Chiralcel OJ, ethanol).

Sources & evidence

ORD record
ord-c36eeb988db045f9bed00ff533e80c0a
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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