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

HRID 13950Notes

Reaction equation

HRID 13950 reaction equation
[Cl:1][C:2]1[C:13]2[CH2:12][CH:11]([CH2:14][NH2:15])[O:10][C:9]=2[C:8]2[CH2:7][CH2:6][CH2:5][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:13]2[CH2:12][CH:11]([CH2:14][NH:15][C:26](=[O:27])[O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:10][C:9]=2[C:8]2[CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 6645Methyl p-toluenesulfonateHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11413423(+/-)-1-(4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine

Product 1

HCID 86598561(+/-)-benzyl (4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamateYield 98.2%

Procedure

Treatment of (±)-1-(4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine (1.11 g, 4.27 mmol) with diisopropylethylamine (1.65 g, 12.8 mmol) followed by benzyl chloroformate (0.87 g, 5.12 mmol) generally according to the procedure described for Intermediate 7 provided 1.5 g (98%) of (±)-benzyl (4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate as a white solid. mp 127-130° C.; Anal. calcd. for C20H20ClNO3: C, 67.13; H, 5.63; N, 3.91. Found: C, 67.03; H, 5.42; N, 3.80. Chiral HPLC separation of (±)-benzyl (4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate (Chiralcel OD, methanol:water 9:1) provided two fractions. Fraction 1 (Rt=12.714 min Chiralcel OD, methanol:water 9:1); Fraction 2 (Rt=16.644 min, Chiralcel OD, methanol:water 9:1).

Sources & evidence

ORD record
ord-dc94ecc71c0c49de99542d899e16895b
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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