Methyl triflate → Trifluoromethanesulfonate

HRID 539618Notes

Reaction equation

HRID 539618 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[NH:13][C:12](=[S:14])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[O:15](C)[S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[N:13]=[C:12]([S:14][CH3:19])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[O-:18][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:17])=[O:15]

Participants

5

Reactant 2

HCID 9526Methyl triflateHCID 58200306HCID 58200306, compound

Product 2

HCID 2758875TrifluoromethanesulfonateHCID 58200253HCID 58200253, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a room temperature solution of (R)-5-(3-fluoro-phenyl)-morpholine-3-thione (128 mg, 0.61 mmol) in methylene chloride (5 mL) under N2 atmosphere was added methyl triflate (0.2 mL, 1.77 mmol). The reaction mixture was stirred at room temperature for 30 minutes, then concentrated under reduced pressure to give crude (R)-3-(3-fluoro-phenyl)-5-methylsulfanyl-3,6-dihydro-2H-[1,4]oxazine as a triflate salt, which was used directly without further purification.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6dfff87db49f4f81a5355e49e33eb76c
Source dataset
uspto-grants-2014_10
Patent number
US08871760B2

Reaction notes

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