2-(Bromomethyl)tetrahydro-2H-pyran → 1-[(2R)-tetrahydrofuran-2-ylmethyl]-5',6',7',8'-tetrahydrospiro[indole-3,3'-naphtho[2,3-b]furan]-2(1'H)-one
Reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:17][CH2:16][CH2:15][O:14]2)(=O)=O)=CC=1.BrCC1CCCCO1.[O:26]1[CH2:30][C:29]2([C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:32][C:31]2=[O:39])[C:28]2[CH:40]=[C:41]3[C:46](=[CH:47][C:27]1=2)[CH2:45][CH2:44][CH2:43][CH2:42]3>>[O:14]1[CH2:15][CH2:16][CH2:17][C@@H:13]1[CH2:12][N:32]1[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:29]2([CH2:30][O:26][C:27]3[CH:47]=[C:46]4[C:41](=[CH:40][C:28]2=3)[CH2:42][CH2:43][CH2:44][CH2:45]4)[C:31]1=[O:39]Participants
Reactant 3
Product 1
Procedure
Following the procedure as described in EXAMPLE 4 and making non-critical variations using (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate to replace 2-(bromomethyl)tetrahydro-2H-pyran, and 5′,6′,7′,8′-tetrahydrospiro[indole-3,3′-naphtho[2,3-b]furan]-2(1H)-one to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2″(1′H)-one, 1-[(2R)-tetrahydrofuran-2-ylmethyl]-5′,6′,7′,8′-tetrahydrospiro[indole-3,3′-naphtho[2,3-b]furan]-2(1H)-one was obtained (80%) as a colorless solid: mp 139-141° C.; 1H NMR (300 MHz, CDCl3) δ 7.32-7.27 (m, 1H), 7.15-7.01 (m, 3H), 6.66 (s, 1H), 6.41 (s, 1H), 4.88 (dd, J=8.9, 0.9 Hz, 1H), 4.63 (dd, J=8.9, 2.5 Hz, 1H), 4.32-4.24 (m, 1H), 4.00-3.69 (m, 4H), 2.75-2.71 (m, 2H), 2.54 (br s, 2H), 2.10-1.86 (m, 3H), 1.78-1.69 (m, 5H); 13C NMR (75 MHz, CDCl3) δ178.0, 158.6, 142.9, 138.8, 132.4, 130.0, 128.6, 126.5, 123.6, 123.4, 123.2, 110.1, 109.5 79.7, 76.9, 68.2, 57.9, 44.6, 29.9, 29.2, 29.0, 25.6, 23.2, 23.0; MS (ES+) m/z 375.9 (M+1).
Sources & evidence
- ORD record
- ord-8668b0662fc841afae607538a60f5725
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415370B2
Reaction notes
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