L-Prolinol → HCID 69282494, compound
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([I:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[OH:14][CH2:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][NH:17]1>CN1CCCC1=O>[I:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:17]3[CH2:18][CH2:19][CH2:20][C@H:16]3[CH2:15][OH:14])=[CH:3][C:4]([CH3:13])=[N:5]2)=[CH:10][CH:9]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A solution of 3.5 g (11.5 mmol) of 4-chloro-7-iodo-2-methylquinoline and 2.92 g (28.8 mmol) of (S)-2-(hydroxymethyl)pyrrolidine in 1-methyl-2-pyrrolidone (50 ml) was heated at 100° C. (oil bath temperature) for 24 h under an argon athmosphere. In order to complete the reaction, 2.2 ml of (S)-2-(hydroxymethyl)pyrrolidine were added and the solution was heated at 100° C. for further 24 h under argon. The solution was then concentrated in a vacuo (4 mbar) at 100° C. The residue was applied to silica gel column with CH2Cl2/MeOH/NH4OH (95:5:0.2) as eluent. Combination of the purified fractions and concentration in vacuo gave 2.7 g (64%) of the desired (S)-[1-(7-iodo-2-methyl-quinolin-4-yl)-pyrrolidin-2-yl]-methanol as light brown solid. ISP mass spectrum, m/e: 369.1 (M+1 calculated for C15H17IN2O: 369).
Workup
- additionwere added
- concentrationThe solution was then concentrated in a vacuo (4 mbar) at 100° C
- concentrationCombination of the purified fractions and concentration in vacuo
Sources & evidence
- ORD record
- ord-bf03cfe148534793a3a5e0c82ffc9f90
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06696467B2
Reaction notes
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