Methyl p-toluenesulfonate → (+/-)-benzyl (5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate

HRID 13955Notes

Reaction equation

HRID 13955 reaction equation
[Cl: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].CC1C=CC(S(OC)(=O)=O)=CC=1>>[Cl: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

5

Reactant 4

HCID 6645Methyl p-toluenesulfonateHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11379089(+/-)-1-(5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine

Product 1

HCID 86598570(+/-)-benzyl (5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamateYield 84%

Procedure

Treatment of (±)-1-(5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine (0.51 g, 1.96 mmol) with diisopropylethylamine (0.76 g, 5.88 mmol) followed by benzyl chloroformate (0.50 g, 2.94 mmol) generally according to the procedure described for Intermediate 7 provided 0.58 g (84%) of (±)-benzyl (5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate as a white solid. mp 118-121° C.; Anal. calcd. for C20H20ClNO3: C, 67.13; H, 5.63; N, 3.91. Found: C, 66.95; H, 5.93; N, 3.82. Chiral HPLC separation of (±)-benzyl (5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate (Chiralpak AD, hexane:isopropanol 9:1) provided two fractions. Fraction 1 (Rt=11.191 min, Chiralpak AD, hexane:isopropanol 9:1); Fraction 2 (Rt=12.735 min, Chiralpak AD, hexane:isopropanol 9:1).

Sources & evidence

ORD record
ord-d9201732c96f4cf8a21d0dfa1a4626d8
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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