(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 71014147, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2(O)[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:3]=1.COCCN(S(F)(F)[F:32])CCOC>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2([F:32])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
To a solution of tert-butyl 4-(4-chloropyridin-2-yl)-4-hydroxypiperidine-1-carboxylate (C3) (0.600 g, 1.92 mmol) in CH2Cl2 (10 mL) cooled to −78° C. was added bis(2-methyoxyethyl)aminosulfur trifluoride (Deoxofluor, 0.71 mL, 3.8 mmol). The reaction was slowly warmed to −40° C. over 3 h, then quenched with water (5 mL) and warmed to RT. The mixture was extracted with CH2Cl2 (2×) and the combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resultant residue was purified via silica gel chromatography eluting with 10-40% ethyl acetate in hexanes to provide tert-butyl 4-(4-chloropyridin-2-yl)-4-fluoropiperidine-1-carboxylate (C4).
Workup
- customquenched with water (5 mL)
- temperaturewarmed to RT
- extractionThe mixture was extracted with CH2Cl2 (2×)
- washthe combined organic fractions were washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resultant residue was purified via silica gel chromatography
- washeluting with 10-40% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-adc3139695bd417d88440a9d86b2ba74
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940765B2
Reaction notes
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