ethyl [3-(hydroxymethyl)-3-(3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate → Ethyl(2-oxo-5',6',7',8'-tetrahydrospiro[indole-3,3'-naphtho[2,3-b]furan]-1(2h)-yl)acetate
Reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:26]O)([C:15]2[C:24]([OH:25])=[CH:23][C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[CH:16]=2)[C:7]1=[O:28])[CH3:2].C(OC(=O)CN1C2C(=CC=CC=2)C(C2C=C3C(=CC=2O)CCC3)(CO)C1=O)C>>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([CH2:26][O:25][C:24]3[CH:23]=[C:22]4[C:17](=[CH:16][C:15]2=3)[CH2:18][CH2:19][CH2:20][CH2:21]4)[C:7]1=[O:28])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
Following the procedure as described in EXAMPLE 1.45, and making non-critical variations using ethyl[3-(hydroxymethyl)-3-(3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate to replace ethyl[3-(6-hydroxy-2,3-dihydro-1H-inden-5-yl)-3-(hydroxymethyl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate, the title compound was obtained (24% in three steps): 1H NMR (300 MHz, CDCl3) δ 7.29 (td, 1H), 7.19 (d, 1H), 7.07 (t, 1H), 6.79 (d, 1H), 6.66 (s, 1H), 6.51 (s, 1H),), 4.91 (d, 1H), 4.67 (d, 1H), 4.52 (ABq, 2H), 4.24 (q, 2H), 2.77-2.51 (m, 4H), 1.77-1.64 (m, 4H), 1.29 (t, 3H); MS (ES+) m/z 378 (M+1).
Sources & evidence
- ORD record
- ord-dbf2302125c240aa814d82d79861a7f5
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700641B2
Reaction notes
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