Triethylamine → HCID 59603864, compound
Reaction equation
[F:1][C:2]1([F:18])[CH2:7][CH2:6][CH2:5][C@H:4]([NH:8][C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[C@H:3]1[OH:17].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C1COCC1>[CH3:26][S:27]([O:17][C@H:3]1[C@H:4]([NH:8][C@@H:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH3:10])[CH2:5][CH2:6][CH2:7][C:2]1([F:18])[F:1])(=[O:29])=[O:28]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 35 °C
Procedure
To a solution of (23) (1.02 g, 4.01 mmol) in THF (20 mL) was added triethyl amine (0.56 mL, 4.01 mmol), followed by methanesulfonyl chloride (0.34 mL, 4.41 mmol). The reaction was allowed to stir at 35° C. overnight. After cooling to room temperature, the reaction mixture was filtered and then concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, 20-60% ethyl acetate in hexanes) to yield (1S,6R)-2,2-difluoro-6-{[(1R)-1-phenylethyl]amino}cyclohexyl methanesulfonate (1.01 g, 3.03 mmol, 76% yield). In a microwave vial, the sulfonate intermediate (1.02 g, 3.07 mmol) was dissolved in THF (15.4 mL) and triethylamine (0.58 mL, 4.15 mmol). The vial was sealed and was heated to 100° C. and was stirred overnight. After cooling to room temperature, the reaction mixture was concentrated under pressure. The resultant residue was directly purified by column chromatography (silica gel, 0-70% ether in hexanes, linear gradient) to yield aziridine 73.
Workup
- temperatureAfter cooling to room temperature
- filtrationthe reaction mixture was filtered
- concentrationconcentrated under reduced pressure
- customThe crude material was purified by column chromatography (silica gel, 20-60% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-036db6c468954b87bc22671475e3863d
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518911B2
Reaction notes
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