Benzyl chloroformate → (+)-benzyl (5-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate

HRID 13927Notes

Reaction equation

HRID 13927 reaction equation
[CH3:1][C:2]1[C:15]2[CH2:14][CH2:13][CH2:12][C:11]=2[C:5]2[O:6][CH:7]([CH2:9][NH2:10])[CH2:8][C:4]=2[CH:3]=1.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]>>[CH3:1][C:2]1[C:15]2[CH2:14][CH2:13][CH2:12][C:11]=2[C:5]2[O:6][CH:7]([CH2:9][NH:10][C:26](=[O:27])[O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:8][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11788932(+/-)-1-(5-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine

Product 1

HCID 86598548(+)-benzyl (5-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamateYield 107.2%

Procedure

Treatment of (±)-1-(5-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine (2.28 g, 11.2 mmol) with diisopropylethylamine (2.16 g, 16.7 mmol) followed by benzyl chloroformate (2.19 g, 12.8 mmol) generally according to the procedure described for Intermediate 15 gave 4.05 g (81%) of (±)-benzyl (5-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate as a white solid. Rf=0.33 (silica, ethyl acetate:hexanes 1:4); mp 109-113° C.; Anal. calcd. for C21H23NO3: C, 74.75; H, 6.87; N, 4.15. Found: C, 74.42; H, 6.91; N, 4.10. Chiral HPLC separation of (±)-benzyl (5-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate (Chiralcel OJ, methanol) provided two fractions. Fraction 1 (Rt=19.001 min, Chiralcel OJ, methanol); Fraction 2 (Rt=23.125 min, Chiralcel OJ, methanol).

Sources & evidence

ORD record
ord-2fbf4d5806a947d19c6f75928cd37008
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

Loading…