Methyl p-toluenesulfonate → (+/-)-Benzyl 2,3-dihydronaphtho[1,2-b]furan-2-ylmethylcarbamate

HRID 13930

Reaction equation

HRID 13930 reaction equation
[O:1]1[CH:5]([CH2:6][NH2:7])[CH2:4][C:3]2[CH:8]=[CH:9][C:10]3[C:15]([C:2]1=2)=[CH:14][CH:13]=[CH:12][CH:11]=3.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>>[O:1]1[CH:5]([CH2:6][NH:7][C:26](=[O:27])[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:4][C:3]2[CH:8]=[CH:9][C:10]3[C:15]([C:2]1=2)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

5

Reactant 4

HCID 6645Methyl p-toluenesulfonateHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11390012(+/-)-1-(2,3-Dihydronaphtho[1,2-b]furan-2-yl)methanamine

Product 1

HCID 69534890(+/-)-Benzyl 2,3-dihydronaphtho[1,2-b]furan-2-ylmethylcarbamateYield 90.4%

Procedure

Treatment of (±)-1-(2,3-dihydronaphtho[1,2-b]furan-2-yl)methanamine (1.19 g, 5.97 mmol) with diisopropylethylamine (0.849 g, 6.57 mmol) followed by benzyl chloroformate (1.07 g, 6.27 mmol) generally according to the procedure described for Intermediate 7 afforded 1.80 g (90%) of (±)-benzyl 2,3-dihydronaphtho[1,2-b]furan-2-ylmethylcarbamate as a white solid. Rf=0.47 (silica, ethyl acetate:hexanes 1:4); mp 110-112° C.; Anal. calcd. for C21H19NO3: C, 75.66; H, 5.74; N, 4.2. Found: C, 75.4; H, 5.57; N, 4.12. Chiral HPLC separation of (±)-benzyl 2,3-dihydronaphtho[1,2-b]furan-2-ylmethylcarbamate (Chiralcel OJ, ethanol) provided two fractions. Fraction 1 (Rt=19.572 min, Chiralcel OJ, ethanol); Fraction 2 (Rt=30.782 min, Chiralcel OJ, ethanol).

Sources & evidence

ORD record
ord-8fd14a0d79cd471bbbed75be34ed846e
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Linked notes

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