(2S)-2-(Trifluoromethyl)oxirane → HCID 118276756, compound

HRID 530612Notes

Reaction equation

HRID 530612 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[S:14](=[O:16])(=[O:15])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[F:17][C:18]([F:23])([F:22])[C@@H:19]1[CH2:21][O:20]1>ClCCl>[F:17][C:18]([F:23])([F:22])[C@@H:19]([OH:20])[CH2:21][N:11]1[CH2:12][CH2:13][S:14](=[O:16])(=[O:15])[CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 7171781(2S)-2-(Trifluoromethyl)oxirane2×HCID 82293051HCID 82293051, compound

Product 1

HCID 118276756HCID 118276756, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 25 mL round-bottomed flask was placed 2-(3-methoxyphenyl)-thiomorpholine-1,1-dioxide (252 mg, 1.04 mmol), followed by (S)-2-(trifluoromethyl)oxirane (129 mg, 1.15 mmol). The reaction mixture was stirred overnight. Reaction was not complete. An additional 100 mg of the (S)-2-(trifluoromethyl)oxirane was added followed by a small amount of dichloromethane. Reaction mixture was stirred at room temperature for an additional 2 h. The crude material was purified by flash chromatography (silica gel, 40 g, 10% to 40% EtOAc in hexanes) afforded (S)-1,1,1-trifluoro-3-[2-(3-methoxyphenyl)-1,1-dioxo-1λ6-thiomorpholin-4-yl]-propan-2-ol (240 mg) as a white foam. (M+H)+=354 m/e.

Workup

  1. customIn a 25 mL round-bottomed flask was placed
  2. customReaction
  3. customReaction mixture
  4. stirringwas stirred at room temperature for an additional 2 h
  5. customThe crude material was purified by flash chromatography (silica gel, 40 g, 10% to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-29314753e66349e58619b51bc31b9b89
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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