Benzyl chloroformate → HCID 86601822, compound

HRID 2115925Notes

Reaction equation

HRID 2115925 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]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>>[CH2:29]([O:28][C:26](=[O:27])[NH:15][CH2:14][CH:11]1[CH2:10][C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:13]=2[O:12]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 68961528HCID 68961528, compound

Product 1

HCID 86601822HCID 86601822, compoundYield 96.1%

Procedure

Treatment of (±)-1-(7-tert-butyl-2,3-dihydro-1-benzofuran-2-yl)methanamine (3.25 g, 13.4 mmol) with diisopropylethylamine (4.34 g, 33.6 mmol) and benzyl chloroformate (2.64 g, 15.5 mmol) generally according to the procedure described for Intermediate 12 gave 4.37 g (96%) of (±)-benzyl(7-tert-butyl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate as a white solid. mp 73-76° C.; Anal. Calcd. for C21H25NO3 C, 74.31; H, 7.42; N, 4.13. Found C, 74.95; H, 7.51; N, 4.18. Chiral HPLC separation of (±)-benzyl(7-tert-butyl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate (Chiralcel OJ, ethanol) provided two fractions. Fraction 1 (Rt=9.100 min, Chiralcel OJ, ethanol); Fraction 2 (Rt=14.428 min, Chiralcel OJ, ethanol).

Sources & evidence

ORD record
ord-1999c5cdcd1a4710aeebc65a97bde8a8
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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