N-methyl-2-pyrrolidone → Methyl 4-[5-[(hydroxy)-(1-methyl-2-oxopyrrolidin-3-yl)methyl]-1-methylindol-3-ylmethyl]-3-methoxybenzoate
Reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[O:24][CH3:25])=[O:2].[CH3:26][N:27]1[CH2:31][CH2:30][CH2:29][C:28]1=[O:32]>>[OH:2][CH:1]([CH:29]1[CH2:30][CH2:31][N:27]([CH3:26])[C:28]1=[O:32])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[O:24][CH3:25]Participants
3
Procedure
Using a similar procedure to that described in Example 1, part d, except starting from methyl 4-(5-formyl-1-methylindol-3-ylmethyl)-3-methoxybenzoate and N-methylpyrrolidone, methyl 4-[5-[(hydroxy)-(1-methyl -2-oxopyrrolidin-3-yl)methyl]-1-methylindol-3-ylmethyl]-3-methoxybenzoate was obtained (40%) as a foam; NMR (300 MHz, DMSO-d6): 1.43-1.65 (m, 1.5H), 1.95 (m, 0.5H), 2.40-2.60 (m, 2.5H), 2.65-2.80 (m, 2H), 2.90-3.25 (m, 1.5H), 3.70 (s, 3H), 3.83 (s, 3H), 3.85-4.08 (m, 5H), 4.92 (d, 0.5H), 5.17 (s, 0.5H), 7.0-7.55 (m, 7H).
Sources & evidence
- ORD record
- ord-ba796a82c9c4435b96bc131b7c79be9b
- Source dataset
- uspto-grants-1991_09
- Patent number
- US05047402
Reaction notes
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