3,4-Dimethylphenol → 8-hydroxy-8-(6-hydroxy-2,3-dihydrobenzofuran-5-yl)-6-(((R)-tetrahydrofuran-2-yl)methyl)-6,8-dihydro-2H-[1,4]dioxino[2,3-f]indol-7(3H)-one
Reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.CC1C=C(O)C=CC=1C.[O:20]1[CH2:24][CH2:23][CH2:22][C@@H:21]1[CH2:25][N:26]1[C:34]2[CH:33]=[C:32]3[O:35][CH2:36][CH2:37][O:38][C:31]3=[CH:30][C:29]=2[C:28](=[O:39])[C:27]1=[O:40].C1(C(C2C=CC=CC=2)N2C3C(=CC=CC=3)C(=O)C2=O)C=CC=CC=1>>[OH:39][C:28]1([C:8]2[C:7]([OH:10])=[CH:6][C:5]3[O:1][CH2:2][CH2:3][C:4]=3[CH:9]=2)[C:29]2[CH:30]=[C:31]3[O:38][CH2:37][CH2:36][O:35][C:32]3=[CH:33][C:34]=2[N:26]([CH2:25][C@H:21]2[CH2:22][CH2:23][CH2:24][O:20]2)[C:27]1=[O:40]Participants
5
Reactant 4
Product 1
Procedure
Following the procedure as described in PREPARATION 6A, and making non-critical variations using 2,3-dihydrobenzofuran-6-ol to replace 3,4-dimethylphenol, and 6-[(2R)-tetrahydrofuran-2-ylmethyl]-2,3-dihydro-6H-[1,4]dioxino[2,3-f]indole-7,8-dione to replace 1-(diphenylmethyl)-1H-indole-2,3-dione, 8-hydroxy-8-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-6-[(2R)-tetrahydrofuran-2-ylmethyl]-2,3,6,8-tetrahydro-7H-[1,4]dioxino[2,3-f]indol-7-one was obtained: Rf 0.45 (ethyl acetate/hexanes, 1/1); MS (ES+) m/z 408.1 (M−17).
Sources & evidence
- ORD record
- ord-bcb7ee01207840f590a54636d7d1da96
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263606B2
Reaction notes
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