1'-[3-(benzyloxy)propyl]-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-one → 1'-(3-hydroxypropyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-one
Reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]2([C:32]3[C:23](=[CH:24][C:25]4[O:30][CH2:29][CH2:28][O:27][C:26]=4[CH:31]=3)[O:22][CH2:21]2)[C:13]1=[O:33])C1C=CC=CC=1.C(OC1C=CC(CN2C3C(=CC=CC=3)C3(COC4C=C5C(=CC3=4)CCO5)C2=O)=CC=1)C1C=CC=CC=1>>[OH:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]2([C:32]3[C:23](=[CH:24][C:25]4[O:30][CH2:29][CH2:28][O:27][C:26]=4[CH:31]=3)[O:22][CH2:21]2)[C:13]1=[O:33]Participants
Reactant 2
Product 1
Procedure
Following the procedure as described in Example 17 and making non-critical variations using 1′-[3-(benzyloxy)propyl]-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one to replace 1′-[4-(benzyloxy)benzyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one, 1′-(3-hydroxypropyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one was obtained (83%): mp 157-158° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.33-7.27 (m, 1H), 7.18-7.15 (m, 1H), 7.08-7.03 (m, 1H), 6.95-6.92 (m, 1H), 6.48 (s, 1H), 6.19 (s 1H), 4.73 (ABq, 2H), 4.19-4.08 (m, 4H), 3.02-3.80 (m, 2H), 3.61-3.55 (m, 2H), 2.98 (d, J=6.0 Hz, 1H), 1.98-1.85 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 178.8, 155.3, 144.6, 141.9, 138.3, 132.4, 128.9, 124.1, 123.6, 120.6, 111.4, 108.5, 99.4, 80.0, 64.5, 63.9, 58.3, 58.1, 36.4, 29.8; MS (ES+) m/z 353.8 (M+1).
Sources & evidence
- ORD record
- ord-6dbdeb141c4848c08da92adc9ee9e101
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415370B2
Reaction notes
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