Trifluoromethanesulfonic anhydride → HCID 59466376, compound
Reaction equation
C(N(CC)C(C)C)(C)C.O[C@H:11]1[CH2:15][CH2:14][NH:13][C:12]1=[O:16].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[Cl:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][CH:42]=1)[NH:39][CH2:38][CH2:37][CH2:36]2>C(Cl)Cl>[Cl:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][CH:42]=1)[N:39]([C@@H:11]1[CH2:15][CH2:14][NH:13][C:12]1=[O:16])[CH2:38][CH2:37][CH2:36]2Participants
Conditions
- Temperature
- -20 °C
Procedure
Prepared using general procedure 57. Under an N2 atmosphere at −20° C., N,N-diisopropylethylamine (1.74 mL, 10.0 mmol) was added dropwise to a solution of (S)-3-hydroxypyrrolidin-2-one (500 mg, 5.0 mmol) in CH2Cl2 (8 mL). Trifluoromethanesulfonic anhydride (0.88 mL, 5.25 mmol) was added dropwise to this solution. Upon completion of addition, the mixture was stirred at −20° C. for 30 min. 6-Chloro-1,2,3,4-tetrahydroquinoline (1.26 g, 7.5 mmol) was added in one portion. The reaction was allowed to warm up to RT overnight. After 18 h, the reaction mixture was washed with saturated aqueous sodium bicarbonate (2×20 mL), brine (20 mL), dried over magnesium sulfate, and concentrated. Purification via silica gel chromatography using 0-30% ethyl acetate in hexane gave (R)-3-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)pyrrolidin-2-one as a colorless oil (150 mg, 12%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=251.3; tR=2.77 min.
Workup
- customPrepared
- additionUpon completion of addition
- temperatureto warm up to RT overnight
- waitAfter 18 h
- washthe reaction mixture was washed with saturated aqueous sodium bicarbonate (2×20 mL), brine (20 mL)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customPurification via silica gel chromatography
Sources & evidence
- ORD record
- ord-20d1f3578af44b45ae3d1647c8bfcd11
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586589B2
Reaction notes
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