Methylumbelliferone → (+/-)-cis-7-Methoxy-1,2,3,3a,4,9b-hexahydro-[1]-benzopyrano[3,4-c]pyrrole

HRID 442783

Reaction equation

HRID 442783 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=O)[O:10]2)=[CH:5][CH:4]=1.CO[CH2:16][N:17](CC1C=CC=CC=1)[CH2:18][Si](C)(C)C>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C@@H:7]3[CH2:18][NH:17][CH2:16][C@@H:8]3[CH2:9][O:10][C:11]=2[CH:12]=1

Participants

3

Reactant 2

HCID 10748MethylumbelliferoneHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

Product 1

HCID 21309105(+/-)-cis-7-Methoxy-1,2,3,3a,4,9b-hexahydro-[1]-benzopyrano[3,4-c]pyrrole

Procedure

From 7-methoxy-coumarin and N-methoxymethyl-N-trimethylsilylmethyl-benzylamine in an analogous manner as described in Examples 1A-C: 1H NMR (300 MHz, CDCl3) δ 1.92 (br s, 1H), 2.60 (m, 1H), 2.81 (m, 2H), 3.17 (q, 1H), 3.29 (dd, 1H), 3.40 (dd, 1H), (s, 3H), 3.78 (t, 1H), 4.10 (dd, 1H), 6.43 (d, 1H), 6.52 (dd, 1H), 7.03 (d, 1H).

Sources & evidence

ORD record
ord-44f751e47dd1492da7d0636846533db6
Source dataset
uspto-grants-1999_04
Patent number
US05891882

Linked notes

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