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
O[CH2:2][C:3]1([C:19]2[C:28]([OH:29])=[CH:27][C:26]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=3[CH:20]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:4]1=[O:18].OC1C=C2C(CCC2)=CC=1C1(CO)C2C(=CC=CC=2)N(CC(OCC)=O)C1=O>>[O:18]=[C:4]1[C:3]2([CH2:2][O:29][C:28]3[CH:27]=[C:26]4[C:21](=[CH:20][C:19]2=3)[CH2:22][CH2:23][CH2:24][CH2:25]4)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]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-81eacaaad24c466e8051e62f7dd331c2
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106087B2
Reaction notes
Loading…