(S)-7-benzyloxy-4-(3-ethoxy-pyrrolidin-1-yl)-2-methyl-quinoline hydrochloride → (S)-4-(3-ethoxy-pyrrolidin-1-yl)-2-methyl-quinolin-7-ol hydrochloride
Reaction equation
[ClH:1].C([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([N:21]3[CH2:25][CH2:24][C@H:23]([O:26][CH2:27][CH3:28])[CH2:22]3)=[CH:15][C:16]([CH3:20])=[N:17]2)=[CH:12][CH:11]=1)C1C=CC=CC=1>CO.[Pd]>[ClH:1].[CH2:27]([O:26][C@H:23]1[CH2:24][CH2:25][N:21]([C:14]2[C:13]3[C:18](=[CH:19][C:10]([OH:9])=[CH:11][CH:12]=3)[N:17]=[C:16]([CH3:20])[CH:15]=2)[CH2:22]1)[CH3:28]Participants
4
Procedure
A solution of 93 mg (0.23 mmol) of (S)-7-Benzyloxy-4-(3-ethoxy-pyrrolidin-1-yl)-2-methyl-quinoline hydrochloride, product of example 28, dissolved in 7 ml of MeOH was treated with 48 mg of palladium on charcoal (10%) and then hydrogenated at RT for 1.5 h until HPLC analysis indicated the completion of the reaction. The catalyst was filtered off, washed with water, and the solution was concentrated in vacuo. The residue was triturated with n hexane/diethyl ether, the solid obtained was filtered off by suction and dried in a high vacuum to give 67 mg (90%) of (S)-4-(3-ethoxy-pyrrolidin-1-yl)-2-methyl-quinolin-7-ol hydrochloride as an off-white solid. ISP mass spectrum, m/e: 273.3 (M+1 calculated for C16H20N2O2: 273).
Workup
- customthe completion of the reaction
- filtrationThe catalyst was filtered off
- washwashed with water
- concentrationthe solution was concentrated in vacuo
- customThe residue was triturated with n hexane/diethyl ether
- customthe solid obtained
- filtrationwas filtered off by suction
- customdried in a high vacuum
Sources & evidence
- ORD record
- ord-f1f40c263c054a8e99f210cac13fe506
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06818767B2
Reaction notes
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