1-(diphenylmethyl)-3-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-1,3-dihydro-2H-indol-2-one → 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[C:2]1([C:22]2[C:23]([OH:31])=[CH:24][C:25]3[O:29][CH2:28][CH2:27][C:26]=3[CH:30]=2)[C:10]2[CH:9]=[C:8]3[O:11][CH2:12][CH2:13][O:14][C:7]3=[CH:6][C:5]=2[N:4]([CH2:15][C@H:16]2[CH2:20][CH2:19][CH2:18][O:17]2)[C:3]1=[O:21].C1(C(C2C=CC=CC=2)N2C3C(=CC=CC=3)C(O)(C3C=CC(OC)=CC=3O)C2=O)C=CC=CC=1>>[OH:31][C:23]1[C:22]([CH:2]2[C:10]3[CH:9]=[C:8]4[O:11][CH2:12][CH2:13][O:14][C:7]4=[CH:6][C:5]=3[N:4]([CH2:15][C@H:16]3[CH2:20][CH2:19][CH2:18][O:17]3)[C:3]2=[O:21])=[CH:30][C:26]2[CH2:27][CH2:28][O:29][C:25]=2[CH:24]=1Participants
Reactant 2
Product 1
Procedure
Following the procedure as described in PREPARATION 12B, and making non-critical variations using 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 to replace 1-(diphenylmethyl)-3-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-1,3-dihydro-2H-indol-2-one, 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 (76%): 1H NMR (300 MHz, CDCl3) δ9.27-9.07 (m, 1H), 6.90-6.81 (m, 1H), 6.74 (s, 1H), 6.72-6.68 (m, 1H), 6.53 (s, 1H), 4.99-4.89 (m, 1H), 4.62-4.45 (m, 2H), 4.38-4.08 (m, 5H), 3.94-3.57 (m, 4H), 3.18-2.89 (m, 2H), 2.06-1.93 (m, 1H), 1.93-1.78 (m, 2H), 1.72-1.55 (m, 1H); MS (ES+) m/z 410.0 (M+1).
Sources & evidence
- ORD record
- ord-2383fbc7a8184d8ca1a22dc017a4f57f
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415370B2
Reaction notes
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