N,N-Diethyl-2,3-dimethylbenzamide → HCID 21100516, compound
Reaction equation
[CH2:1]([CH:3]1[N:7]([CH2:8][CH2:9][C:10]#[N:11])[CH:6]([CH2:12][OH:13])[CH:5]([CH3:14])[CH2:4]1)[CH3:2].C(N(CC)[C:18](=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=1[CH3:26])C>>[CH2:1]([CH:3]1[N:7]([CH2:8][CH2:9][C:10]2[NH:11][C:18](=[O:27])[C:19]3[C:20]([CH:26]=2)=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=3)[CH:6]([CH2:12][OH:13])[CH:5]([CH3:14])[CH2:4]1)[CH3:2]Participants
Procedure
In the same manner as in the method described in Tetrahedron Lett., Vol. 32, No. 30, pp. 3727-3730 (1991), ethyl 5-ethyl-3-methylpyrrolidine-2-carboxylate hydrochloride is obtained. In the same manner as in Example 1b (a) and using ethyl 5-ethyl-3-methylpyrrolidine-2-carboxylate hydrochloride, ethyl 1-tert-butoxycarbonyl-5-ethyl-3-methylpyrrolidine-2-carboxylate is obtained. In the same manner as in Example 1b (b) and using ethyl 1-tert-butoxycarbonyl-5-ethyl-3-methylpyrrolidine-2-carboxylate, 1-tert-butoxycarbonyl-5-ethyl-2-hydroxymethyl-3-methylpyrrolidine is obtained. In the same manner as in Example 1b (c) and using 1-tert-butoxycarbonyl-5-ethyl-2-hydroxymethyl-3-methylpyrrolidine, 5-ethyl-2-hydroxymethyl-3-methylpyrrolidine hydrochloride is obtained. In the same manner as in Example 1b (d) and using 5-ethyl-2-hydroxymethyl-3-methylpyrrolidine hydrochloride, 3-(5-ethyl-2-hydroxymethyl-3-methylpyrrolidin-1-yl)propionitrile is obtained. In the same manner as in Example 1b (e) and using 3-(5-ethyl-2-hydroxymethyl-3-methylpyrrolidin-1-yl)propionitrile and N,N-diethyl-2,3-dimethylbenzamide, 3-[2-(5-ethyl-2-hydroxymethyl-3-methylpyrrolidin-1-yl)ethyl]-5-methyl-2H-isoquinolin-1-one is obtained.
Sources & evidence
- ORD record
- ord-edbf18561fd3419b975998d8ab7cd10a
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07812178B2
Reaction notes
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